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ST-1936
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	1210-81-7 ;
PubChem CID	9921064;
ChemSpider	8096699;
UNII	4R5ZNV2CHC;
ChEMBL	ChEMBL365751;
CompTox Dashboard (EPA)	DTXSID001045649 ;
Chemical and physical data
Formula	C13H17ClN2
Molar mass	236.74 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(CCN(C)C)C2=CC(Cl)=CC=C2N1;
	InChI InChI=1S/C13H17ClN2/c1-9-11(6-7-16(2)3)12-8-10(14)4-5-13(12)15-9/h4-5,8,15H,6-7H2,1-3H3; Key:KSYMELKKLOFABL-UHFFFAOYSA-N;

ST-1936 (2-methyl-5-chloro-N,N-dimethyltryptamine) is a tryptamine derivative which is used in scientific research. It acts as a selective 5-HT₆ receptor agonist, with a K_i of 13 nM, and much weaker action at 5-HT_2B and 5-HT₇ subtypes. In animal studies it has been found to increase dopamine and noradrenaline mediated signalling but decreases glutamatergic transmission, and has antidepressant effects.^[1]^[2]^[3]^[4]

References

^ Valentini V, Frau R, Bordi F, Borsini F, Di Chiara G (March 2011). "A microdialysis study of ST1936, a novel 5-HT6 receptor agonist". Neuropharmacology. 60 (4): 602–8. doi:10.1016/j.neuropharm.2010.12.006. PMID 21185318. S2CID 26758667.
^ Riccioni T, Bordi F, Minetti P, Spadoni G, Yun HM, Im BH, et al. (July 2011). "ST1936 stimulates cAMP, Ca2+, ERK1/2 and Fyn kinase through a full activation of cloned human 5-HT6 receptors". European Journal of Pharmacology. 661 (1–3): 8–14. doi:10.1016/j.ejphar.2011.04.028. PMID 21549693.
^ Tassone A, Madeo G, Schirinzi T, Vita D, Puglisi F, Ponterio G, et al. (September 2011). "Activation of 5-HT6 receptors inhibits corticostriatal glutamatergic transmission". Neuropharmacology. 61 (4): 632–7. doi:10.1016/j.neuropharm.2011.05.004. PMID 21619890. S2CID 24612187.
^ Scheggi S, Marchese G, Borsini F, Bordi F, De Montis MG (October 2011). "Effects of the 5-HT(6) receptor agonist ST 1936 on depression- and anhedonia-like experimental models". Behavioural Brain Research. 224 (1): 35–43. doi:10.1016/j.bbr.2011.05.019. PMID 21645553. S2CID 6270975.

[1] Valentini V, Frau R, Bordi F, Borsini F, Di Chiara G (March 2011). "A microdialysis study of ST1936, a novel 5-HT6 receptor agonist". Neuropharmacology. 60 (4): 602–8. doi:10.1016/j.neuropharm.2010.12.006. PMID 21185318. S2CID 26758667.

[2] Riccioni T, Bordi F, Minetti P, Spadoni G, Yun HM, Im BH, et al. (July 2011). "ST1936 stimulates cAMP, Ca2+, ERK1/2 and Fyn kinase through a full activation of cloned human 5-HT6 receptors". European Journal of Pharmacology. 661 (1–3): 8–14. doi:10.1016/j.ejphar.2011.04.028. PMID 21549693.

[3] Tassone A, Madeo G, Schirinzi T, Vita D, Puglisi F, Ponterio G, et al. (September 2011). "Activation of 5-HT6 receptors inhibits corticostriatal glutamatergic transmission". Neuropharmacology. 61 (4): 632–7. doi:10.1016/j.neuropharm.2011.05.004. PMID 21619890. S2CID 24612187.

[4] Scheggi S, Marchese G, Borsini F, Bordi F, De Montis MG (October 2011). "Effects of the 5-HT(6) receptor agonist ST 1936 on depression- and anhedonia-like experimental models". Behavioural Brain Research. 224 (1): 35–43. doi:10.1016/j.bbr.2011.05.019. PMID 21645553. S2CID 6270975.

[1]

[2]

[3]

[4]

Tryptamines
Tryptamines	1-Methylpsilocin 2-HO-NMT 2-Me-DET 2-Methyl-5-HT 2,N,N-TMT 4,5-DHP-DMT 4-AcO-DALT 4-AcO-DET 4-AcO-DiPT 4-AcO-DPT 4-AcO-EPT 4-AcO-MALT 4-AcO-MET 4-AcO-MiPT 4-AcO-NMT 4-AcO-TMT 4-F-5-MeO-DMT 4-HO-5-MeO-DMT 4-HO-DALT 4-HO-DBT 4-HO-DET 4-HO-DiPT 4-HO-DPT 4-HO-DSBT 4-HO-EPT 4-HO-MALT 4-HO-MET 4-HO-McPT 4-HO-McPeT 4-HO-MiPT 4-HO-MPT 4-HO-MsBT 4-HO-NALT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-HO-TMT 4-HT 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-PrO-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Bromo-DMT 5-CT 5-Chloro-DMT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-MET 5-HO-DiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NMT 5-MeO-pyr-T 5-MeO-NBpBrT 5-MeO-T-NBOMe 5-MeS-DMT 5-Methoxytryptamine (5-MT; mexamine) 5-Methyl-DMT 5-Methyltryptamine 5-MT-NB3OMe 5-(Nonyloxy)tryptamine 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-DHT 5,7-DHT 6-Fluoro-DMT 6-MeO-DMT 7-Methyl-DMT Acetryptine (5-AT) Aeruginascin (4-PO-TMT) AGH-107 AGH-192 AH-494 ALiPT Alpertine Baeocystin (4-PO-NMT) Benzotript (4-chlorobenzoyl-L-tryptophan) Bufotenidine (5-HTQ) Bufotenin (5-HO-DMT) Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EMDT EPT Ethocybin (4-PO-DET) FGIN-127 FGIN-143 FT-104 HIOC Idalopirdine Indolylethylfentanyl Indorenate Iprocin (4-HO-DiPT) Lespedamine MET Methylbutyltryptamine Miprocin (4-HO-MiPT) MiPT MPT Milipertine MS-245 MSBT N-Feruloylserotonin (moschamine) NET NMT Norbaeocystin (4-PO-T) NTBT O-4310 O-Pivalylbufotenine Oxypertine PiPT Psilacetin (O-acetylpsilocin; 4-AcO-DMT) Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Pyr-T RS134-49 Serotonin (5-HT) Solypertine ST-1936 Tryptamine Tryptophan Yuremamine Z2876442907
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301
α-Alkyltryptamines	2,α-DMT 4-HO-αMT 4-HO-MPMI (lucigenol) 4-Me-αET 4-Me-αMT 5-Chloro-αMT 5-Ethoxy-αMT 5-Fluoro-αET 5-Fluoro-αMT 5-iPrO-αMT 5-MeO-α,N,N-TMT 5-MeO-αET 5-MeO-αMT 5-MeO-MPMI 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Methyl-αET α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT) α-Methyltryptophan (αMTP) α,N-DMT (N-methyl-αMT) α,N,N-TMT α,N,O-TMS αET (etryptamine) αMT AL-37350A (4,5-DHP-αMT) BNC-210 BW-723C86 CP-135807 IPAP (α,N-DPT) MPMI
Triptans	Almotriptan Donitriptan Eletriptan Frovatriptan L-694247 Rizatriptan Sumatriptan Zolmitriptan
Cyclized tryptamines	Bay R 1531 Ciclindole Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD) Flucindole Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH, 9-Me-BC, β-carboline (norharman), harmaline, harmalol, harmane, harmine, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids and related (e.g., DM-506 (ibogaminalog), ibogaine, ibogamine, noribogaine, tabernanthalog, tabernanthine) Metralindole NDTDI PHA-57378 PNU-22394 PNU-181731 RU-28306 Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine)
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT AAZ-A-154 AL-34662 AL-38022A BRL-54443 CP-94253 EMD-386088 I-32 IAL Latrepirdine LY-367265 Pirlindole (R)-69 (3IQ) Ro60-0175 Ro60-0213 RU-24,969 Sertindole SN-22 Substituted benzofurans (e.g., 3-APB, 5-MeO-DiBF, BPAP, dimemebfe, mebfap) Tepirindole Tetrindole Triptans (e.g., avitriptan, LY-334370, naratriptan) VER-3323 VU6067416 YM-348

Clinical data

ATC code	none
Identifiers
IUPAC name 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	1210-81-7^Y
PubChem CID	9921064
ChemSpider	8096699
UNII	4R5ZNV2CHC
ChEMBL	ChEMBL365751
CompTox Dashboard (EPA)	DTXSID001045649
Chemical and physical data
Formula	C₁₃H₁₇ClN₂
Molar mass	236.74 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=C(CCN(C)C)C2=CC(Cl)=CC=C2N1
InChI InChI=1S/C13H17ClN2/c1-9-11(6-7-16(2)3)12-8-10(14)4-5-13(12)15-9/h4-5,8,15H,6-7H2,1-3H3 Key:KSYMELKKLOFABL-UHFFFAOYSA-N

Infrastructure tools to support an effective radiation oncology learning health system

See also

References