N-sec-Butyltryptamine

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

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

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 threes 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