Potency and safety analysis of hemp-derived delta-9 products: The hemp vs. cannabis demarcation problem

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An assortment of several designer drugs.

Designer drugs are structural or functional analogues of controlled substances that are designed to mimic the pharmacological effects of the parent drug while avoiding detection or classification as illegal. Many of the older designer drugs (research chemicals) are structural analogues of psychoactive tryptamines or phenethylamines but there are many other chemically unrelated new psychoactive substances that can be considered part of the designer drug group.[1][2][3][4] Designer drugs can also include substances that are not psychoactive in effect, such as analogues of controlled anabolic steroids and other performance and image enhancing drugs (PIEDs), including nootropics, weight loss drugs and erectile dysfunction medications. The pharmaceutical activities of these compounds might not be predictable based strictly upon structural examination. Many of the substances have common effects while structurally different or different effects while structurally similar due to SAR paradox. As a result of no real official naming for some of these compounds, as well as regional naming, this can all lead to potentially hazardous mix ups for users.[5] The following list is not exhaustive.

Androgens

Androgenic anabolic steroids have approved medical uses as well as used illicitly as performance-enhancing drugs to build muscle mass and strength. Anabolic steroids that have been designed to evade detection in sport doping tests are known as "designer steroids".[6][7]

Testosterone based

DHT based

Estranes

SARMs

Selective androgen receptor modulators (SARMs) are a novel class of androgen receptor ligands. They are intended to maintain the desirable muscle building effects of anabolic steroids while reducing undesirable androgenic actions (e.g., increased risk of prostate cancer). SARMs that are more selective in their action could potentially be used for a broader range of clinical indications other than the relatively limited legitimate uses that anabolic steroids are currently approved for.[8]

Empathogens

Empathogens are a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of MDMA. Users of empathogens say the drugs often produce feelings of empathy, love, and emotional closeness to others.

MDxx

Substituted methylenedioxyphenethylamines (MDxx) are a large chemical class of derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelics, and/or stimulants, as well as entheogens.

Benzofurans

Benzofurans are similar in structure to MD(M)A but differ in that the methylenedioxy groups have been modified, removing one of the two oxygens in the methylenedioxy ring to render a benzofuran ring.

Miscellaneous polycyclic phenethylamines

Indane and tetralin-type phenethylamines are vaguely related to their amphetamine analogues.

Only one non-tryptamine indole has been sold, 5-IT. It shows strong MAOI activity.

  • 5-IT, 5-API, PAL-571

Tryptamines

Drugs containing the tryptamine moiety are typically substrates for the serotonin receptors, in keeping with their close structural resemblance to serotonin, a neurotransmitter.

  • αET, α-Ethyltryptamine, "Monase"
  • 5-MeO-αET, α,O-Diethylserotonin
  • αMT, α-Methyltryptamine, "Indopan"
  • 5-MeO-αMT, α,O-Dimethylserotonin

Amphetamines

Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions.

  • 4-BA, 4-Bromoamphetamine, PBA
  • 4-CA, 4-Chloroamphetamine, PCA
  • 4-CMA, 4-Chloromethamphetamine, PCMA
  • 4-FA, 4-Fluoroamphetamine, PFA
  • 4-FMA, 4-Fluoromethamphetamine, PFMA
  • 4-Fluoroselegiline, 4F-Deprenyl
  • 4-MA, 4-Methylamphetamine, PAL-313
  • 4-MeOA, 4-Methoxyamphetamine, PMA, 4-MeO-A, "Death"
  • 4-MeOMA, 4-Methoxymethamphetamine, PMMA, 4-MeO-MA
  • 4-MTA, 4-Methylthioamphetamine
  • Methamnetamine, N-Methyl-PAL-287, Methylnaphetamine, MNT, MNA
  • MMA, 3-Methoxy-4-Methylamphetamine
  • 3-FEA, 3F-Ethamphetamine, 3-Fluoroethamphetamine

Phenethylamines

Drugs containing the phenethylamine moiety bear close structural resemblance to dopamine but substitution on the benzene ring gives rise to drugs with a much higher affinity for serotonin receptors.

Dissociatives

Dissociatives are a class of hallucinogens which distort perceptions of sight and sound and produce feelings of detachment - dissociation - from the environment and self. This is done through reducing or blocking signals to the conscious mind from other parts of the brain. Although many kinds of drugs are capable of such action, dissociatives are unique in that they do so in such a way that they produce hallucinogenic effects, which may include sensory deprivation, dissociation, hallucinations, and dream-like states or trances. Some, which are nonselective in action and affect the dopamine and/or opioid systems, may be capable of inducing euphoria. Many dissociatives have general depressant effects and can produce sedation, respiratory depression, analgesia, anesthesia, and ataxia, as well as cognitive and memory impairment and amnesia.

Arylcyclohexylamines

Arylcyclohexylamines are the oldest and most widely used dissociatives. The class includes the well known anaesthetic, ketamine.

Diarylethylamines

Diarylethylamines began to appear on grey markets only as recently as 2013.

Misc

Nootropics

Central nervous system stimulants

Systematic reviews and meta-analyses of clinical research using low doses of certain central nervous system stimulants found that these drugs may enhance cognition in healthy people.[13][14][15] In particular, the classes of stimulants that demonstrate possible cognition-enhancing effects in humans have evidence in vitro as direct agonists or indirect agonists of dopamine receptor D1 or adrenoceptor A2.[13][14][16][17] Relatively high doses of stimulants cause cognitive deficits.[16][17]

  • Amphetamine – systematic reviews and meta-analyses report that low-dose amphetamine may improve cognitive functions (e.g., inhibitory control, episodic memory, working memory, and aspects of attention) in healthy people and in individuals with ADHD.[13][14][15][17] A 2014 systematic review noted that low doses of amphetamine also improve memory consolidation, in turn leading to improved recall of information in non-ADHD youth.[15] It also improves task saliency (motivation to perform a task) and performance on tedious tasks that required a high degree of effort.[14][16][17]
  • Caffeine – a meta-analysis found an increase in alertness and attentional performance.[18][16]
  • Eugeroics (armodafinil and modafinil) – are classified as "wakefulness-promoting agents"; modafinil may increase alertness, particularly in sleep-deprived individuals, and may improve reasoning and problem solving in non-ADHD youth.[15] In a systematic review of small, preliminary studies where the effects of modafinil were examined, when simple psychometric assessments were considered, modafinil intake enhanced executive function.[19] Modafinil does not improve mood or motivation in sleep-deprived or non-sleep deprived individuals.[20]
  • Methylphenidate – a benzylpiperidine derivative that may improve working memory, episodic memory, and inhibitory control, aspects of attention, and planning latency in healthy people.[13][15] It also may improve task saliency and performance on tedious tasks.[17] At above optimal doses, methylphenidate has off–target effects that decrease learning.[21]
  • Nicotine – has been associated with improved alertness, attention, memory, and motor performance, according to a meta-analysis.[22] However, a 2020 systematic review raised concerns about potential conflicts of interest, noting industry funding in many studies and inconsistent results regarding nicotine's cognitive effects. This review found that over half of the studies published after 2010 had tobacco industry affiliations, often undisclosed.[23]

Racetams

Racetams, such as piracetam, oxiracetam, phenylpiracetam, and aniracetam, are often marketed as cognitive enhancers and sold over the counter.[24][25] A 2019 study found that piracetam supplements sold in the United States were inaccurately labeled.[25] Racetams are often referred to as nootropics, but this property is not well established in humans, and nootropics are not consistently found in all racetams.[26] The racetams have poorly understood mechanisms, although piracetam and aniracetam are known to act as positive allosteric modulators of AMPA receptors and appear to modulate cholinergic systems.[27]

According to the FDA,

Piracetam is not a vitamin, mineral, amino acid, herb or other botanical, or dietary substance for use by humans to supplement the diet by increasing the total dietary intake. Further, piracetam is not a concentrate, metabolite, constituent, extract or combination of any such dietary ingredient. [...] Accordingly, these products are drugs, under section 201(g)(1)(C) of the Act, 21 U.S.C. § 321(g)(1)(C), because they are not foods and they are intended to affect the structure or any function of the body. Moreover, these products are new drugs as defined by section 201(p) of the Act, 21 U.S.C. § 321(p), because they are not generally recognized as safe and effective for use under the conditions prescribed, recommended, or suggested in their labeling.[28]

Cholinergics

Some supposed nootropic substances are compounds and analogues of choline, a precursor of acetylcholine (a neurotransmitter) and phosphatidylcholine (a structural component of cell membranes).

  • Alpha-GPC – L-alpha glycerylphosphorylcholine has been studied only in the context of cognitive performance alongside other substances such as caffeine.[29]
  • Choline bitartrate – Choline bitartrate is a tartaric acid salt containing choline (41% choline by molecular weight). One meta-analysis found choline bitartrate to be ineffective at improving any measure of cognitive performance.[30]
  • Citicoline – Compound consisting of choline and cytidine. A meta-analysis found that it may be effective for improving memory and learning in older people with mild cognitive decline, and in people recovering from a stroke.[31][32]

Examples

PDE5 inhibitors

PDE5 inhibitors are typically used to treat pulmonary hypertension and erectile dysfunction.[33]

Peptides

GHRH analogues

GHRH analogues stimulate the release of growth hormone.

Growth hormone secretagogue receptor agonists

Agonists of the growth hormone secretagogue receptor stimulate the release of growth hormone through the ghrelin receptor.

Others

Piperazines

Piperazine containing designer drugs have effects similar to MDMA (ecstasy). This class of drugs are mimics of serotonin that activate 5-HT receptor subtypes that release norepinephrine and dopamine.

Psychedelics

A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics tend to affect and explore the mind in ways that result in the experience being qualitatively different from those of ordinary consciousness. The psychedelic experience is often compared to non-ordinary forms of consciousness such as trance, meditation, yoga, religious ecstasy, dreaming and even near-death experiences.

Lysergamides

Lysergamides are amide derivatives of the alkaloid lysergic acid.

Tryptamines

Drugs containing the tryptamine moiety are typically substrates for the serotonin receptors, in keeping with their close structural resemblance to serotonin, a neurotransmitter.

Benzofurans

2C-x

2C-x class of psychedelics are 2,5-dimethoxy-phenethylamine derivatives.

NBxx

NNxx

DOx

The DOx family of psychedelics are also known as "substituted amphetamines" as they contain the amphetamine backbone but are substituted on the benzene ring. This gives rise to serotonin agonists similar to the 2C-X class but more resistant to elimination in the body.

Sedatives

Sedatives are substances that induces sedation by reducing irritability or excitement. At higher doses they may result in slurred speech, staggering gait, poor judgment, and slow, uncertain reflexes. Doses of sedatives such as benzodiazepines, when used as a hypnotic to induce sleep, tend to be higher than amounts used to relieve anxiety, whereas only low doses are needed to provide a peaceful effect. Sedatives can be misused to produce an overly-calming effect. In the event of an overdose or if combined with another sedative, many of these drugs can cause unconsciousness and even death.

Alcohols

Opioids

Opioids have pharmacologic actions resembling morphine and other components of opium.

N-(2C)-fentanyl

Benzodiazepines

Thienodiazepines

GHB analogues

Methaqualone analogues

Misc

Stimulants

Stimulants produce a variety of different kinds of effects by enhancing the activity of the central and peripheral nervous systems. Common effects, which vary depending on the substance and dosage in question, may include enhanced alertness, awareness, wakefulness, endurance, productivity, and motivation, increased arousal, locomotion, heart rate, and blood pressure, and the perception of a diminished requirement for food and sleep.

Amphetamines

Amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions.

Cathinones

Cathinones include some stimulants and entactogens, which are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions.

Pyrrolidines and Pyrrolidinophenones

Pyrrolidines are amphetamines with a pyrrolidine group. Pyrrolidinophenones (also called Pyrovalerones) are cathinones (βk-amphetamines) with a pyrrolidine group.

Thiophenes

Thiophenes are stimulant drugs which are analogues of amphetamine or cathinone where the phenyl ring has been replaced by thiophene.

Tropanes and Piperidines

Tropane alkaloids occur in plants of the families erythroxylaceae (including coca). Piperidine and its derivatives are ubiquitous building blocks in the synthesis of many pharmaceuticals and fine chemicals.

Oxazolidines

Oxazolidines are a five-membered ring compounds consisting of three carbons, a nitrogen, and an oxygen. The oxygen and NH are the 1 and 3 positions, respectively. In oxazolidine derivatives, there is always a carbon between the oxygen and the nitrogen.

Phenylmorpholines

Phenylmorpholines are a class of stimulants containing a phenethylamine skeleton in which the terminal amine is incorporated into a morpholine ring.

Misc

Synthetic cannabinoids

Agonists of the central cannabinoid receptor type 1 mimic the behavioral effects of cannabis.

Classical cannabinoids

Cyclohexeylphenol cannabinoids

Miscellaneous cannabinoids

Indazole based

Indazole containing cannabinoid receptor agonists include:

Indole based

Indole containing cannabinoid receptor agonists include:

Quinolinylindoles

Benzoylindoles

Adamantoylindoles

Naphthoylindoles

Phenylacetylindoles

Others

See also

References

  1. ^ "EMCDDA–Europol 2013 Annual Report on the information exchange, risk assessment and control of new psychoactive substances (implementation of Council Decision 2005/387/JHA)". EMCDDA. July 2014. Retrieved 8 August 2014.
  2. ^ "EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)". EMCDDA. May 2013. Retrieved 8 August 2014.
  3. ^ "EMCDDA–Europol 2011 Annual Report on the (information exchange, risk assessment and control of new psychoactive substances) implementation of Council Decision 2005/387/JHA". EMCDDA. April 2012. Retrieved 8 August 2014.
  4. ^ "EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA". EMCDDA. May 2011. Retrieved 8 August 2014.
  5. ^ Shimizu E, Watanabe H, Kojima T, Hagiwara H, Fujisaki M, Miyatake R, et al. (January 2007). "Combined intoxication with methylone and 5-MeO-MIPT". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 31 (1): 288–291. doi:10.1016/j.pnpbp.2006.06.012. PMID 16876302. S2CID 29089303.
  6. ^ Kazlauskas R (2009). "Designer Steroids". Doping in Sports. Handbook of Experimental Pharmacology. Vol. 195. pp. 155–85. doi:10.1007/978-3-540-79088-4_7. ISBN 978-3-540-79087-7. PMID 20020364.
  7. ^ Abushareeda W, Fragkaki A, Vonaparti A, Angelis Y, Tsivou M, Saad K, et al. (March 2014). "Advances in the detection of designer steroids in anti-doping". Bioanalysis. 6 (6): 881–896. doi:10.4155/bio.14.9. PMID 24702116.
  8. ^ Zhang X, Sui Z (February 2013). "Deciphering the selective androgen receptor modulators paradigm". Expert Opinion on Drug Discovery. 8 (2): 191–218. doi:10.1517/17460441.2013.741582. PMID 23231475. S2CID 2584722.
  9. ^ "N-[1-(2,3-Dihydro-1,4-benzodioxin-6-yl)propan-2-yl]-N-methylhydroxylamine". PubChem. U.S. National Library of Medicine.
  10. ^ a b Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (1 July 2015). "A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products". Forensic Toxicology. 33 (2): 244–259. doi:10.1007/s11419-015-0268-7. PMC 4525202. PMID 26257833.
  11. ^ "2-FDCK". VBCHEMICALS LTD. 2023. Retrieved 21 May 2024.
  12. ^ Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–632. doi:10.1002/dta.1620. PMID 24678061.
  13. ^ a b c d Spencer RC, Devilbiss DM, Berridge CW (June 2015). "The cognition-enhancing effects of psychostimulants involve direct action in the prefrontal cortex". Biological Psychiatry. 77 (11): 940–950. doi:10.1016/j.biopsych.2014.09.013. PMC 4377121. PMID 25499957.
  14. ^ a b c d Ilieva IP, Hook CJ, Farah MJ (June 2015). "Prescription Stimulants' Effects on Healthy Inhibitory Control, Working Memory, and Episodic Memory: A Meta-analysis". Journal of Cognitive Neuroscience. 27 (6): 1069–1089. doi:10.1162/jocn_a_00776. PMID 25591060. S2CID 15788121.
  15. ^ a b c d e Bagot KS, Kaminer Y (April 2014). "Efficacy of stimulants for cognitive enhancement in non-attention deficit hyperactivity disorder youth: a systematic review". Addiction. 109 (4): 547–557. doi:10.1111/add.12460. PMC 4471173. PMID 24749160.
  16. ^ a b c d Wood S, Sage JR, Shuman T, Anagnostaras SG (January 2014). "Psychostimulants and cognition: a continuum of behavioral and cognitive activation". Pharmacological Reviews. 66 (1): 193–221. doi:10.1124/pr.112.007054. PMC 3880463. PMID 24344115.
  17. ^ a b c d e Malenka RC, Nestler EJ, Hyman SE, Holtzman DM (2015). "14: Higher Cognitive Function and Behavioral Control". Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (3 ed.). New York: McGraw-Hill Medical. ISBN 9780071827706.
  18. ^ Camfield DA, Stough C, Farrimond J, Scholey AB (August 2014). "Acute effects of tea constituents L-theanine, caffeine, and epigallocatechin gallate on cognitive function and mood: a systematic review and meta-analysis". Nutrition Reviews. 72 (8): 507–522. doi:10.1111/nure.12120. PMID 24946991.
  19. ^ Battleday RM, Brem AK (November 2015). "Modafinil for cognitive neuroenhancement in healthy non-sleep-deprived subjects: A systematic review". European Neuropsychopharmacology. 25 (11): 1865–1881. doi:10.1016/j.euroneuro.2015.07.028. PMID 26381811. S2CID 23319688.
  20. ^ Mohamed AD (2017). "Does modafinil improve cognitive functioning in healthy individuals?". In ter Meulen R, Hall W, Mohammed AD (eds.). Rethinking Cognitive Enhancement. Oxford University Press. p. 116. ISBN 9780198727392.
  21. ^ Urban KR, Gao WJ (2014). "Performance enhancement at the cost of potential brain plasticity: neural ramifications of nootropic drugs in the healthy developing brain". Frontiers in Systems Neuroscience. 8: 38. doi:10.3389/fnsys.2014.00038. PMC 4026746. PMID 24860437.
  22. ^ Heishman SJ, Kleykamp BA, Singleton EG (July 2010). "Meta-analysis of the acute effects of nicotine and smoking on human performance". Psychopharmacology. 210 (4): 453–469. doi:10.1007/s00213-010-1848-1. PMC 3151730. PMID 20414766.
  23. ^ Pasetes, Sarah V.; Ling, Pamela M.; Apollonio, Dorie E. (January 2020). "Cognitive performance effects of nicotine and industry affiliation: a systematic review". Substance Abuse: Research and Treatment. 14: 117822182092654. doi:10.1177/1178221820926545. ISSN 1178-2218. PMC 7271274. PMID 32547048.
  24. ^ Cohen PA, Avula B, Wang YH, Zakharevich I, Khan I (June 2021). "Five Unapproved Drugs Found in Cognitive Enhancement Supplements". Neurology. Clinical Practice. 11 (3): e303–e307. doi:10.1212/CPJ.0000000000000960. PMC 8382366. PMID 34484905.
  25. ^ a b Cohen PA, Zakharevich I, Gerona R (March 2020). "Presence of Piracetam in Cognitive Enhancement Dietary Supplements". JAMA Internal Medicine. 180 (3): 458–459. doi:10.1001/jamainternmed.2019.5507. PMC 6902196. PMID 31764936.
  26. ^ Malenka RC, Nestler EJ, Hyman SE (2009). Sydor A, Brown RY (eds.). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2 ed.). New York: McGraw-Hill Medical. p. 454. ISBN 9780071481274.
  27. ^ Gualtieri F, Manetti D, Romanelli MN, Ghelardini C (2002). "Design and study of piracetam-like nootropics, controversial members of the problematic class of cognition-enhancing drugs". Current Pharmaceutical Design. 8 (2): 125–138. doi:10.2174/1381612023396582. PMID 11812254.
  28. ^ John Gridley (30 August 2010). "FDA Warning Letter: Unlimited Nutrition". Office of Compliance, Center for Food Safety and Applied Nutrition, Inspections, Compliance, Enforcement, and Criminal Investigations, US Food and Drug Administration. Archived from the original on 12 January 2017. Retrieved 5 April 2016.
  29. ^ Parker AG, Byars A, Purpura M, Jäger R (September 21, 2015). "The effects of alpha-glycerylphosphorylcholine, caffeine or placebo on markers of mood, cognitive function, power, speed, and agility". Journal of the International Society of Sports Nutrition. 12 (Suppl 1): P41. doi:10.1186/1550-2783-12-S1-P41. ISSN 1550-2783. PMC 4595381.
  30. ^ Lippelt DP, van der Kint S, van Herk K, Naber M (June 24, 2016). "No Acute Effects of Choline Bitartrate Food Supplements on Memory in Healthy, Young, Human Adults". PLOS ONE. 11 (6): e0157714. Bibcode:2016PLoSO..1157714L. doi:10.1371/journal.pone.0157714. PMC 4920398. PMID 27341028.
  31. ^ Fioravanti M, Buckley AE (September 2006). "Citicoline (Cognizin) in the treatment of cognitive impairment". Clinical Interventions in Aging. 1 (3): 247–251. doi:10.2147/ciia.2006.1.3.247. PMC 2695184. PMID 18046877.
  32. ^ Franco-Maside A, Caamaño J, Gómez MJ, Cacabelos R (October 1994). "Brain mapping activity and mental performance after chronic treatment with CDP-choline in Alzheimer's disease". Methods and Findings in Experimental and Clinical Pharmacology. 16 (8): 597–607. PMID 7760585.
  33. ^ Dhaliwal, Armaan; Gupta, Mohit (2023), "PDE5 Inhibitors", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID 31751033, retrieved 2023-10-24
  34. ^ "Public Notification: "RigiRx Plus" Contains Undeclared Drug Ingredient". US FDA. 20 April 2012. Retrieved 15 August 2014.
  35. ^ "Difluoromethylenedioxybenzylpiperazine". PubChem. U.S. National Library of Medicine.
  36. ^ Brandt SD, Kavanagh PV, Westphal F, Pulver B, Schwelm HM, Whitelock K, et al. (August 2022). "Analytical profile, in vitro metabolism and behavioral properties of the lysergamide 1P-AL-LAD". Drug Testing and Analysis. 14 (8): 1503–1518. doi:10.1002/dta.3281. PMC 9546273. PMID 35524430.
  37. ^ "4-HO-DALT". Isomerdesign.
  38. ^ "5-MeO-NiPT". Isomerdesign.
  39. ^ "N-[2-(1H-Indol-3-yl)ethyl]-N-methylcyclopropanamine". PubChem. U.S. National Library of Medicine.
  40. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  41. ^ Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, et al. (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. PMID 15537358.
  42. ^ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
  43. ^ Vandeputte MM, Cannaert A, Stove CP (November 2020). "In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances". Archives of Toxicology. 94 (11): 3819–3830. doi:10.1007/s00204-020-02855-7. hdl:1854/LU-8687070. PMID 32734307. S2CID 220881657.
  44. ^ Oldenhof S, Ten Pierick A, Bruinsma J, Eustace S, Hulshof J, van den Berg J, Hoitink M (January 2020). "Identification of a novel fentanyl analog: p-Hydroxy-butyrylfentanyl". Drug Testing and Analysis. 12 (1): 152–155. doi:10.1002/dta.2695. PMID 31518047.
  45. ^ Blanckaert P, Balcaen M, Vanhee C, Risseeuw M, Canfyn M, Desmedt B, et al. (September 2021). "Analytical characterization of "etonitazepyne," a new pyrrolidinyl-containing 2-benzylbenzimidazole opioid sold online". Drug Testing and Analysis. 13 (9): 1627–1634. doi:10.1002/dta.3113. hdl:1854/LU-8737722. PMID 34145779. S2CID 235479893.
  46. ^ Krotulski AJ, Mohr AL, Papsun DM, Logan BK (January 2018). "Metabolism of novel opioid agonists U-47700 and U-49900 using human liver microsomes with confirmation in authentic urine specimens from drug users". Drug Testing and Analysis. 10 (1): 127–136. doi:10.1002/dta.2228. PMID 28608586.
  47. ^ "2-(3,4-Dichlorophenyl)-N-[(1S,2S)-2-(dimethylamino)cyclohexyl]-N-methylacetamide". ChemSpider.
  48. ^ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
  49. ^ "Explore N-(2C-C)-Fentanyl | PiHKAL · info". isomerdesign.com.
  50. ^ "Explore N-(2C-D)-Fentanyl | PiHKAL · info". isomerdesign.com.
  51. ^ "Explore N-(2C-E)-Fentanyl | PiHKAL · info". isomerdesign.com.
  52. ^ "Explore N-(2C-G)-Fentanyl | PiHKAL · info". isomerdesign.com.
  53. ^ "Explore N-(2C-H)-Fentanyl | PiHKAL · info". isomerdesign.com.
  54. ^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
  55. ^ "Explore N-(2C-IP)-Fentanyl | PiHKAL · info". isomerdesign.com.
  56. ^ "Explore N-(2C-N)-Fentanyl | PiHKAL · info". isomerdesign.com.
  57. ^ "Explore N-(2C-P) fentanyl | PiHKAL · info". isomerdesign.com.
  58. ^ "Explore N-(2C-T)-Fentanyl | PiHKAL · info". isomerdesign.com.
  59. ^ "Explore N-(2C-T-2)-Fentanyl | PiHKAL · info". isomerdesign.com.
  60. ^ "Explore N-(2C-T-4)-Fentanyl | PiHKAL · info". isomerdesign.com.
  61. ^ "Explore N-(2C-T-7)-Fentanyl | PiHKAL · info". isomerdesign.com.
  62. ^ "Explore N-(2C-TFM)-Fentanyl | PiHKAL · info". isomerdesign.com.
  63. ^ Trigg S, Wells JM, McGann J, Bock S, Holman A, Harrison SM, et al. (September 2022). "The alprazolam analogue 4'-chloro deschloroalprazolam identified in seized capsules". Drug Testing and Analysis. 14 (9): 1672–1680. doi:10.1002/dta.3325. PMID 35666014. S2CID 249382539.
  64. ^ "ChemIDplus - 7-Bromo-5-phenyl-1,2-dihydro-2H-1,4-benzodiazepin-2-one". chem.nlm.nih.gov.
  65. ^ Andronati SA, Zin'kovskiĭ VG, Totrova MI, Golovenko NI, Stankevich EA, Zhuk OV (January 1992). "[Biokinetics of a new prodrug gidazepam and its metabolite]". Biulleten' Eksperimental'noi Biologii I Meditsiny. 113 (1): 45–47. PMID 1356504.
  66. ^ "2-FMC" (PDF). SWGDRUG. 2013. Retrieved 19 August 2014.
  67. ^ "2-Methylethcathinone". Cayman Chemical. Retrieved 6 September 2015.
  68. ^ "2,4-Dimethylethcathinone". PubChem. U.S. National Library of Medicine.
  69. ^ "2,4-Dimethylmethcathinone". PubChem. U.S. National Library of Medicine.
  70. ^ a b c d e f Kaizaki-Mitsumoto A, Noguchi N, Yamaguchi S, Odanaka Y, Matsubayashi S, Kumamoto H, et al. (January 2016). "Three 25-NBOMe-type drugs, three other phenethylamine-type drugs (25I-NBMD, RH34, and escaline), eight cathinone derivatives, and a phencyclidine analog MMXE, newly identified in ingredients of drug products before they were sold on the drug market". Forensic Toxicology. 34 (1): 108–114. doi:10.1007/s11419-015-0293-6. ISSN 1860-8965. S2CID 45890497.
  71. ^ "3-Ethylethcathinone". Cayman Chemical. Retrieved 29 September 2015.
  72. ^ "3-MeOMC". Cayman Chemical. Retrieved 27 December 2014.
  73. ^ "3-MEC" (PDF). SWGDRUG. 2013. Retrieved 19 August 2014.
  74. ^ "3-MMC Powder". VBCHEMICALS LTD. 2023. Retrieved 5 May 2024.
  75. ^ "CID 82100370". PubChem. U.S. National Library of Medicine.
  76. ^ Harm S (11 April 1967). "US Patent 3313687 - Appetite-suppressing and weight reducing composition".
  77. ^ "4F-IVP". Cayman Chemical. Retrieved 29 September 2015.
  78. ^ "4-FPD". Cayman Chemical. Retrieved 7 April 2015.
  79. ^ a b c d e Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, et al. (October 2014). "Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, α-PHPP and α-POP, with 11 newly distributed designer drugs in illegal products". Forensic Science International. 243: 1–13. doi:10.1016/j.forsciint.2014.03.013. PMID 24769262.
  80. ^ "4-methyl-N,N-DMC". Cayman Chemical. Retrieved 7 April 2015.
  81. ^ Weiß JA, Taschwer M, Kunert O, Schmid MG (March 2015). "Analysis of a new drug of abuse: cathinone derivative 1-(3,4-dimethoxyphenyl)-2-(ethylamino)pentan-1-one". Journal of Separation Science. 38 (5): 825–828. doi:10.1002/jssc.201401052. PMID 25545103.
  82. ^ "N-Isopropylpentedrone". PubChem. U.S. National Library of Medicine.
  83. ^ "1-(2,3-Dihydro-1H-inden-5-yl)-2-(ethylamino)pentan-1-one". PubChem. U.S. National Library of Medicine.
  84. ^ Gaspar H, Bronze S, Ciríaco S, Queirós CR, Matias A, Rodrigues J, et al. (July 2015). "4F-PBP (4'-fluoro-α-pyrrolidinobutyrophenone), a new substance of abuse: Structural characterization and purity NMR profiling". Forensic Science International. 252: 168–176. doi:10.1016/j.forsciint.2015.05.003. PMID 26005857.
  85. ^ Shintani-Ishida K, Nakamura M, Tojo M, Idota N, Ikegaya H (May 2015). "Identification and quantification of 4′-methoxy-α-pyrrolidinobutiophenone (4-MeOPBP) in human plasma and urine using LC–TOF-MS in an autopsy case". Forensic Toxicology. 33 (2): 348–354. doi:10.1007/s11419-015-0281-x. S2CID 24716021.
  86. ^ "1-(2,3-Dihydro-1H-inden-5-yl)-2-pyrrolidin-1-ylbutan-1-one". PubChem. U.S. National Library of Medicine.
  87. ^ "α-PBT". Cayman Chemical. Retrieved 27 December 2014.
  88. ^ "1-(2,3-Dihydro-1H-inden-5-yl)-2-pyrrolidin-1-ylhexan-1-one". PubChem. U.S. National Library of Medicine.
  89. ^ "3,4-MDPHP". Cayman Chemical. Retrieved 7 April 2015.
  90. ^ "PV-8". Forendex. Southern Association of Forensic Scientists. Retrieved 13 August 2014.
  91. ^ "4-MeO-PV-9". Cayman Chemical. Retrieved 27 December 2014.
  92. ^ "PV-10". Cayman Chemical. Retrieved 7 April 2015.
  93. ^ "5-Methyl-2-phenylmorpholine". PubChem. U.S. National Library of Medicine.
  94. ^ "3-Fluorophenetrazine Hydrochloride". www.trc-canada.com.
  95. ^ "4-Ethyl-3-methyl-2-phenylmorpholine". PubChem. U.S. National Library of Medicine.
  96. ^ "3-Ethyl-2-phenylmorpholine". PubChem. U.S. National Library of Medicine.
  97. ^ Power JD, Scott KR, Gardner EA, Curran McAteer BM, O'Brien JE, Brehon M, et al. (January 2014). "The syntheses, characterization and in vitro metabolism of nitracaine, methoxypiperamide and mephtetramine". Drug Testing and Analysis. 6 (7–8): 668–675. doi:10.1002/dta.1616. PMID 24574100.
  98. ^ Odoardi S, Mestria S, Biosa G, Arfè R, Tirri M, Marti M, Strano Rossi S (August 2021). "Metabolism study and toxicological determination of mephtetramine in biological samples by liquid chromatography coupled with high-resolution mass spectrometry". Drug Testing and Analysis. 13 (8): 1516–1526. doi:10.1002/dta.3044. PMC 8453881. PMID 33835674.
  99. ^ "2-[Bis(4-fluorophenyl)methylsulfinyl]-N-methylacetamide". PubChem. U.S. National Library of Medicine.
  100. ^ "EG-2201". Cayman Chemical. Retrieved 27 October 2015.
  101. ^ a b Mogler L, Franz F, Wilde M, Huppertz LM, Halter S, Angerer V, et al. (September 2018). "Phase I metabolism of the carbazole-derived synthetic cannabinoids EG-018, EG-2201, and MDMB-CHMCZCA and detection in human urine samples". Drug Testing and Analysis. 10 (9): 1417–1429. doi:10.1002/dta.2398. PMID 29726116.
  102. ^ "Methyl (S)-2-(9-(cyclohexylmethyl)-9H-carbazole-3-carboxamido)-3,3-dimethylbutanoate". PubChem. U.S. National Library of Medicine.
  103. ^ a b c Qian Z, Jia W, Li T, Hua Z, Liu C (January 2017). "Identification and analytical characterization of four synthetic cannabinoids ADB-BICA, NNL-1, NNL-2, and PPA(N)-2201". Drug Testing and Analysis. 9 (1): 51–60. doi:10.1002/dta.1990. PMID 27239006.
  104. ^ Krotulski AJ, Mohr AL, Kacinko SL, Fogarty MF, Shuda SA, Diamond FX, et al. (September 2019). "4F-MDMB-BINACA: A New Synthetic Cannabinoid Widely Implicated in Forensic Casework". Journal of Forensic Sciences. 64 (5): 1451–1461. doi:10.1111/1556-4029.14101. PMID 31260580. S2CID 195770459.
  105. ^ Haschimi B, Mogler L, Halter S, Giorgetti A, Schwarze B, Westphal F, et al. (September 2019). "Detection of the recently emerged synthetic cannabinoid 4F-MDMB-BINACA in "legal high" products and human urine specimens". Drug Testing and Analysis. 11 (9): 1377–1386. doi:10.1002/dta.2666. PMID 31228224. S2CID 195260495.
  106. ^ "5-Chloro AKB48". PubChem. U.S. National Library of Medicine.
  107. ^ "5F-MN-18". Forendex. Southern Association of Forensic Scientists. Retrieved 12 August 2014.
  108. ^ "5F-NPB-22". Cayman Chemical. Retrieved 9 May 2015.
  109. ^ "5F-SDB-005". Forendex. Southern Association of Forensic Scientists. Retrieved 13 August 2014.
  110. ^ "AMB". Forendex. Southern Association of Forensic Scientists. Retrieved 13 August 2014.
  111. ^ Krotulski AJ, Mohr AL, Diamond FX, Logan BK (January 2020). "Detection and characterization of the new synthetic cannabinoid APP-BINACA in forensic casework". Drug Testing and Analysis. 12 (1): 136–144. doi:10.1002/dta.2698. PMID 31788963.
  112. ^ Nakajima JI, Takahashi M, Uemura N, Seto T, Fukaya H, Suzuki J, et al. (November 2014). "Identification of N,N-bis(1-pentylindol-3-yl-carboxy)naphthylamine (BiPICANA) found in an herbal blend product in the Tokyo metropolitan area and its cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays". Forensic Toxicology. 33: 84–92. doi:10.1007/s11419-014-0253-6. S2CID 25165289.
  113. ^ Pulver B, Schönberger T, Weigel D, Köck M, Eschenlohr Y, Lucas T, et al. (August 2022). "Structure elucidation of the novel synthetic cannabinoid Cumyl-Tosyl-Indazole-3-Carboxamide (Cumyl-TsINACA) found in illicit products in Germany". Drug Testing and Analysis. 14 (8): 1387–1406. doi:10.1002/dta.3261. PMID 35338591. S2CID 247713676.
  114. ^ Pulver, Benedikt; Fischmann, Svenja; Gallegos, Ana; Christie, Rachel (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403.
  115. ^ "Ethyl (2S)-2-[[1-[(4-fluorophenyl)methyl]indazole-3-carbonyl]amino]-3-methylbutanoate". PubChem. U.S. National Library of Medicine.
  116. ^ "FUB-NPB-22". Cayman Chemical. Retrieved 9 May 2015.
  117. ^ "NPB-22". Cayman Chemical. Retrieved 9 May 2015.
  118. ^ Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA". ACS Chemical Neuroscience. 6 (9): 1546–1559. doi:10.1021/acschemneuro.5b00112. PMID 26134475.
  119. ^ "[1-(5-Fluoropentyl)indol-3-yl]-pyrrolidin-1-ylmethanone". PubChem. U.S. National Library of Medicine.
  120. ^ Qian Z, Hua Z, Liu C, Jia W (January 2016). "Four types of cannabimimetic indazole and indole derivatives, ADB-BINACA, AB-FUBICA, ADB-FUBICA, and AB-BICA, identified as new psychoactive substances". Forensic Toxicology. 34 (1): 133–143. doi:10.1007/s11419-015-0297-2. PMC 4705129. PMID 26793280.
  121. ^ Deventer MH, Van Uytfanghe K, Vinckier IM, Reniero F, Guillou C, Stove CP (September 2022). "A new cannabinoid receptor 1 selective agonist evading the 2021 "China ban": ADB-FUBIATA". Drug Testing and Analysis. 14 (9): 1639–1644. doi:10.1002/dta.3285. hdl:1854/LU-01GQ757043ZZ4MNSKMZ52FAKJ1. PMID 35570246. S2CID 248812121.
  122. ^ Pasin D, Nedahl M, Mollerup CB, Tortzen C, Reitzel LA, Dalsgaard PW (September 2022). "Identification of the synthetic cannabinoid-type new psychoactive substance, CH-PIACA, in seized material". Drug Testing and Analysis. 14 (9): 1645–1651. doi:10.1002/dta.3333. PMC 9544820. PMID 35687099.
  123. ^ "CBL-018". Cayman Chemical. Retrieved 26 October 2015.
  124. ^ Wiley JL, Lefever TW, Cortes RA, Marusich JA (September 2014). "Cross-substitution of Δ9-tetrahydrocannabinol and JWH-018 in drug discrimination in rats". Pharmacology, Biochemistry, and Behavior. 124: 123–128. doi:10.1016/j.pbb.2014.05.016. PMC 4150816. PMID 24887450.
  125. ^ Takayama K, Noguchi Y, Aoki S, Takayama S, Yoshida M, Asari T, et al. (February 2015). "Identification of the minimum peptide from mouse myostatin prodomain for human myostatin inhibition". Journal of Medicinal Chemistry. 58 (3): 1544–1549. doi:10.1021/jm501170d. PMID 25569186.