N-Propyltryptamine

N-Propyltryptamine
Clinical data
Other names	NPT; N-n-Propyltryptamine
Drug class	Serotonin receptor modulator
ATC code	None;
Identifiers
	IUPAC name N-[2-(1H-indol-3-yl)ethyl]propan-1-amine;
PubChem CID	45605;
ChemSpider	41495;
Chemical and physical data
Formula	C13H18N2
Molar mass	202.301 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCNCCC1=CNC2=CC=CC=C21;
	InChI InChI=1S/C13H18N2/c1-2-8-14-9-7-11-10-15-13-6-4-3-5-12(11)13/h3-6,10,14-15H,2,7-9H2,1H3; Key:KBFBIAGUZWNRFI-UHFFFAOYSA-N;

N-Propyltryptamine (NPT) is a serotonin receptor modulator of the tryptamine family related to N-methyltryptamine (NMT).¹²³ According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), NPT is not known to have been tested in humans.¹ It acts as a serotonin receptor agonist in the rat uterus and stomach strip, with slightly lower potency than dimethyltryptamine (DMT).⁴³ However, in contrast to DMT and NMT, NPT did not cause central effects in dogs.²⁵ It is said to be less toxic than dipropyltryptamine (DPT) in rodents.¹ The chemical synthesis of NPT has been described.¹⁶ NPT was first described in the scientific literature by Speeter and Anthony by 1954.²⁴³⁵ Subsequently, the drug was described by Shulgin in TiHKAL in 1997.¹

References

Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "The normal-propylamine NPT has been made by the oxalylamide route, with the amide having with a mp 179–181 °C (75%) from benzene and NPT hydrochloride mp 186–187 °C (33%) from MeOH/benzene. An attempt to make NPT by the alkyl halide procedure failed. Using these same ratios of reactants, there was the formation of a sizable quantity of DPT with appreciable unreacted tryptamine presence (T:NPT:DPT/1:5:4). A recycling under the same conditions gave T:NPT:DPT/0:3:7) and a third cycle gave only DPT, but with a loss of almost 90% of the material presumably to quaternary salt formation. Interestingly NPT is less toxic than DPT in experimental mice, but has not been assayed yet in man."
Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. Little is known of the monosubstituted tryptamines. N-Methyltryptamine has been mentioned as a minor component in Anadenanthera spp. It has also been identified in the bark of Virola theiodora (Cassidy et al., 1969), a plant that is one of the principal sources of the carbo-line psychotomimetics. In comparison with dimethyltryptamine, mono-methyltryptamine produces less central stimulation in the dog, and the monopropyl homolog [(XXIII), R = n-C3H7] is without activity (Conner, 1954). The n-hexyl homolog [(XXIII), R = n-C6H13] has been found inactive in a limited number of subjects (Szara, 1967). The mono-tert-butyl derivative [(XXIII), R = t-C4H9) has the reputation of oral activity (see above discussion concerning anonymous street knowledge), but dosage details are not known.
Barlow RB, Khan I (March 1959). "Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations". British Journal of Pharmacology and Chemotherapy. 14 (1): 99–107. doi:10.1111/j.1476-5381.1959.tb00934.x. PMC 1481812. PMID 13651585.
Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". British Journal of Pharmacology and Chemotherapy. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.
Speeter ME, Anthony WC (1954). "The Action of Oxalyl Chloride on Indoles: A New Approach to Tryptamines". Journal of the American Chemical Society. 76 (23): 6208–6210. Bibcode:1954JAChS..76R6208S. doi:10.1021/ja01652a113. ISSN 0002-7863. (5) Studies by Dr. Nolen Connor of our Laboratories indicate the hydroxyl group is not essential for activity on the central nervous system as 3-(2-dimethylaminoethyl) indole [(DMT)] has grossly the same action in the dog as bufotenine [(5-HO-DMT)]. In contrast, 3-(2-methylaminoethyl)-indole [(NMT)] has slight activity while 3-(2-n-propylaminoethyl)-indole [(NPT)] produced no apparent symptoms.
Jensen N (2004). Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens (PhD thesis). Georg-August-Universität zu Göttingen.

External links

[TiHKAL-1] Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "The normal-propylamine NPT has been made by the oxalylamide route, with the amide having with a mp 179–181 °C (75%) from benzene and NPT hydrochloride mp 186–187 °C (33%) from MeOH/benzene. An attempt to make NPT by the alkyl halide procedure failed. Using these same ratios of reactants, there was the formation of a sizable quantity of DPT with appreciable unreacted tryptamine presence (T:NPT:DPT/1:5:4). A recycling under the same conditions gave T:NPT:DPT/0:3:7) and a third cycle gave only DPT, but with a loss of almost 90% of the material presumably to quaternary salt formation. Interestingly NPT is less toxic than DPT in experimental mice, but has not been assayed yet in man."

[Shulgin1976-2] Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. Little is known of the monosubstituted tryptamines. N-Methyltryptamine has been mentioned as a minor component in Anadenanthera spp. It has also been identified in the bark of Virola theiodora (Cassidy et al., 1969), a plant that is one of the principal sources of the carbo-line psychotomimetics. In comparison with dimethyltryptamine, mono-methyltryptamine produces less central stimulation in the dog, and the monopropyl homolog [(XXIII), R = n-C3H7] is without activity (Conner, 1954). The n-hexyl homolog [(XXIII), R = n-C6H13] has been found inactive in a limited number of subjects (Szara, 1967). The mono-tert-butyl derivative [(XXIII), R = t-C4H9) has the reputation of oral activity (see above discussion concerning anonymous street knowledge), but dosage details are not known.

[BarlowKhan1959-3] Barlow RB, Khan I (March 1959). "Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations". British Journal of Pharmacology and Chemotherapy. 14 (1): 99–107. doi:10.1111/j.1476-5381.1959.tb00934.x. PMC 1481812. PMID 13651585.

[Vane1959-4] Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". British Journal of Pharmacology and Chemotherapy. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.

[SpeeterAnthony1954-5] Speeter ME, Anthony WC (1954). "The Action of Oxalyl Chloride on Indoles: A New Approach to Tryptamines". Journal of the American Chemical Society. 76 (23): 6208–6210. Bibcode:1954JAChS..76R6208S. doi:10.1021/ja01652a113. ISSN 0002-7863. (5) Studies by Dr. Nolen Connor of our Laboratories indicate the hydroxyl group is not essential for activity on the central nervous system as 3-(2-dimethylaminoethyl) indole [(DMT)] has grossly the same action in the dog as bufotenine [(5-HO-DMT)]. In contrast, 3-(2-methylaminoethyl)-indole [(NMT)] has slight activity while 3-(2-n-propylaminoethyl)-indole [(NPT)] produced no apparent symptoms.

[Jensen2004-6] Jensen N (2004). Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens (PhD thesis). Georg-August-Universität zu Göttingen.

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External links