N-sec-Butyltryptamine

N-sec-Butyltryptamine

Clinical data
Other names	NsBT; NSBT
Routes of administration	Oral [1] [2]
Drug class	Psychoactive drug [1] [2]
ATC code	None
Pharmacokinetic data
Duration of action	"Short" [1]
Identifiers
IUPAC name N-[2-(1H-indol-3-yl)ethyl]butan-2-amine
PubChem CID	24839509
ChemSpider	23993854
Chemical and physical data
Formula	C14H20N2
Molar mass	216.328 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(C)NCCC1=CNC2=CC=CC=C21
InChI InChI=1S/C14H20N2/c1-3-11(2)15-9-8-12-10-16-14-7-5-4-6-13(12)14/h4-7,10-11,15-16H,3,8-9H2,1-2H3 Key:WDWNZOAFDWLAGZ-UHFFFAOYSA-N

N-sec-Butyltryptamine (NsBT) is a psychoactive drug of the tryptamine family related to psychedelics like dimethyltryptamine (DMT). ^{[1] [2]}

Use and effects

NsBT was briefly described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). ^[1] According to Shulgin, NsBT is active at a dose of 25 to 75 mg orally and has a short-lived duration. ^{[1] [2]} Its effects included a generalized and somewhat diffuse intoxication, intellectual excitement, modest sensory enhancements, and "a lot of erotic horniness". ^[1] However, no "plus-three" ratings occurred on the Shulgin Rating Scale. ^[1]

Shulgin has said that along with N-tert-butyltryptamine (NtBT), it is one of only two N-mono-substituted tryptamines with known psychoactivity. ^[1] He also said that N-mono-substituted tryptamines might be GHB-like intoxicants devoid of psychedelic effects. ^[1] However, N-methyltryptamine (NMT) has been reported to produce psychedelic effects. ^{[1] [3] [4]}

Chemistry

Analogues

Analogues of NsBT include N-methyltryptamine (NMT), N-ethyltryptamine (NET), N-isopropyltryptamine (NiPT), N-benzyltryptamine (NBnT), and N-methyl-N-sec-butyltryptamine (MsBT), among others. ^[1]

See also

• Substituted tryptamine

References

1. Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. https://erowid.org/library/books_online/tihkal/tihkal49.shtml "The two geometric isomers, mono-isobutyl and mono-sec-butyl tryptamines are best called NIBT and NSBT. They also have been made by the oxalylamide route and the hydrochloride salts melt at 150-151 °C and 175-177 °C resp. Interestingly, NSBT is one of the two mono-substituted tryptamines that just might have CNS activity. It has shown a generalized and somewhat diffuse intoxication with several studies covering the 25 to 75 milligram range. Short lived, intellectual excitement with some modest sensory enhancements. Promising, and a lot of erotic horniness, but no plus threes, yet." [...] "The tertiary-butyl analogue, NTBT, is the remaining mono-substituted tryptamine that just might have psychotropic potential. In the 5 to 20 milligram area, there is a light-headed intoxication that is a totally pleasant buzz, but nothing more profound than that. Wouldn't it be fascination of it turned out that all of the mono-tryptamines (the NRT's) were GHB-like intoxicants, and totally devoid of psychedelic activity. That would be a true challenge to the SAR crowd. I was told many years ago that NTBT was extremely potent when smoked, but I never received any particulars, and I must leave that as a baseless rumor."
2. Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4.
3. Nen (4 December 2011). Entheogenic effects of NMT from Acacia. Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011 (PDF). Archived from the original on 5 April 2025. Retrieved 15 April 2025.
4. Nen (13 July 2013). NMT: A Spatial Hallucinogen With Therapeutic Applications. Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013.

External links

• NSBT - Isomer Design