Isamide

Isamide
Clinical data
Other names	N-(1-Chloroacetyl)-5-methoxytryptamine
Drug class	Serotonin receptor antagonist
Identifiers
	IUPAC name 2-chloro-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide;
CAS Number	21424-91-9;
PubChem CID	192991;
ChemSpider	167480;
CompTox Dashboard (EPA)	DTXSID10175697 ;
Chemical and physical data
Formula	C13H15ClN2O2
Molar mass	266.73 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC2=C(C=C1)NC=C2CCNC(=O)CCl;
	InChI InChI=1S/C13H15ClN2O2/c1-18-10-2-3-12-11(6-10)9(8-16-12)4-5-15-13(17)7-14/h2-3,6,8,16H,4-5,7H2,1H3,(H,15,17); Key:UCLPNTKRPMTACI-UHFFFAOYSA-N;

Isamide, also known as N-chloroacetyl-5-methoxytryptamine, is a serotonin receptor antagonist and the N-chloro acetyl derivative of 5-methoxytryptamine.^[1]^[2]^[3] It was first described in the scientific literature by 1969 and was first pharmacologically characterized by 1979.^[4]^[2]

References

^ Frohlich PF, Meston CM (2000). "Evidence that serotonin affects female sexual functioning via peripheral mechanisms". Physiology & Behavior. 71 (3–4): 383–393. doi:10.1016/s0031-9384(00)00344-9. PMID 11150571.
^ ^a ^b Huidobro-Toro JP, Huidobro F, Ruiz M (June 1979). "N-Chloroacetyl 5-methoxytryptamine (isamide): a selective antagonist of 5-hydroxytryptamine in the rat uterus". The Journal of Pharmacy and Pharmacology. 31 (6): 371–374. doi:10.1111/j.2042-7158.1979.tb13525.x. PMID 39134.
^ Huidobro-Toro JP, Foree B (February 1980). "Dual agonist-antagonist effects of 5-hydroxytryptamine (5-HT) in the guinea pig ileum: evidence for a selective receptor desensitization effect". European Journal of Pharmacology. 61 (4): 335–345. doi:10.1016/0014-2999(80)90072-2. PMID 6102916.
^ Kobayashi T, Spande TF, Aoyagi H, Witkop B (July 1969). "Tricyclic analogs of melatonin". Journal of Medicinal Chemistry. 12 (4): 636–638. doi:10.1021/jm00304a017. PMID 5793155.

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[FrohlichMeston2000-1] Frohlich PF, Meston CM (2000). "Evidence that serotonin affects female sexual functioning via peripheral mechanisms". Physiology & Behavior. 71 (3–4): 383–393. doi:10.1016/s0031-9384(00)00344-9. PMID 11150571.

[Huidobro-ToroHuidobroRuiz1979-2] Huidobro-Toro JP, Huidobro F, Ruiz M (June 1979). "N-Chloroacetyl 5-methoxytryptamine (isamide): a selective antagonist of 5-hydroxytryptamine in the rat uterus". The Journal of Pharmacy and Pharmacology. 31 (6): 371–374. doi:10.1111/j.2042-7158.1979.tb13525.x. PMID 39134.

[Huidobro-ToroForee1980-3] Huidobro-Toro JP, Foree B (February 1980). "Dual agonist-antagonist effects of 5-hydroxytryptamine (5-HT) in the guinea pig ileum: evidence for a selective receptor desensitization effect". European Journal of Pharmacology. 61 (4): 335–345. doi:10.1016/0014-2999(80)90072-2. PMID 6102916.

[KobayashiSpandeAoyagi1969-4] Kobayashi T, Spande TF, Aoyagi H, Witkop B (July 1969). "Tricyclic analogs of melatonin". Journal of Medicinal Chemistry. 12 (4): 636–638. doi:10.1021/jm00304a017. PMID 5793155.

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v t e 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