N-Propyltryptamine

N-Propyltryptamine (NPT) is a serotonin receptor modulator of the tryptamine family related to N-methyltryptamine (NMT).^[1]^[2]^[3] 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).^[4]^[3] However, in contrast to DMT and NMT, NPT did not cause central effects in dogs.^[2]^[5] It is said to be less toxic than dipropyltryptamine (DPT) in rodents.^[1] The chemical synthesis of NPT has been described.^[1]^[6] NPT was first described in the scientific literature by Speeter and Anthony by 1954.^[2]^[4]^[3]^[5] Subsequently, the drug was described by Shulgin in TiHKAL in 1997.^[1]

Other namesNPT; N-n-Propyltryptamine

Drug classSerotonin receptor modulator

ATC code

None

PubChem CID

45605

Quick facts Clinical data, Other names ...

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

References

[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."
[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.
[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.
[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.
[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.
[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.

N-Propyltryptamine

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