O-Acetylbufotenine

O-Acetylbufotenine
Clinical data
Other names	3-(2-(dimethylamino)ethyl)-1H-indol-5-yl acetate; 5-Acetoxy-DMT; 5-Acetoxy-N,N-dimethyltryptamine; 5-AcO-DMT; 3-(2-(Dimethylamino)ethyl]-1H-indol-5-yl acetate
Identifiers
	IUPAC name [3-[2-(dimethylamino)ethyl]-1H-indol-5-yl] acetate;
CAS Number	16977-50-7;
PubChemCID	15480709;
ChemSpider	23194786;
ChEMBL	ChEMBL111000;
CompTox Dashboard(EPA)	DTXSID701345666;
Chemical and physical data
Formula	C14H18N2O2
Molar mass	246.310g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)OC1=CC2=C(C=C1)NC=C2CCN(C)C;
	InChI InChI=1S/C14H18N2O2/c1-10(17)18-12-4-5-14-13(8-12)11(9-15-14)6-7-16(2)3/h4-5,8-9,15H,6-7H2,1-3H3; Key:BZFGYTBVFYYKOK-UHFFFAOYSA-N;

O-Acetylbufotenine(5-AcO-DMT,bufotenine acetate) is atryptaminederivative which producespsychedelic-appropriate responding in animal studies. It is an acylated derivative ofbufoteninewith higherlipophilicitythat allows it to cross theblood–brain barrier;once inside the brain, it is metabolised to bufotenine.^[1]^[2]^[3]It also acts directly as an agonist at 5-HT_1Aand 5-HT_1Dreceptors.^[4]

References[edit]

^Shulgin & Shulgin. TiHKAL #19. 5-HO-DMT
^Gessner PK, Dankova JB (January 1975). "Brain Bufotenine from Administered Acetylbufotenine: Comparison of Its Tremorgenic Activity with That of N,N-Dimethyltryptamine and 5-Methoxy-N,N-Dimethyltryptamine".Pharmacologist.17(2): 259.
^Winter JC, Amorosi DJ, Rice KC, Cheng K, Yu AM (September 2011)."Stimulus control by 5-methoxy-N,N-dimethyltryptamine in wild-type and CYP2D6-humanized mice".Pharmacology, Biochemistry, and Behavior.99(3): 311–5.doi:10.1016/j.pbb.2011.05.015.PMC3129464.PMID 21624387.
^Glennon RA, Hong SS, Bondarev M, Law H, Dukat M, Rakhi S, Power P, Fan E, Kinneau D, Kamboj R, Teitler M, Herrick-Davis K, Smith C (January 1996). "Binding of O-alkyl derivatives of serotonin at human 5-HT1D beta receptors".Journal of Medicinal Chemistry.39(1): 314–22.doi:10.1021/jm950498t.PMID 8568822.

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[1] Shulgin & Shulgin. TiHKAL #19. 5-HO-DMT

[2] Gessner PK, Dankova JB (January 1975). "Brain Bufotenine from Administered Acetylbufotenine: Comparison of Its Tremorgenic Activity with That of N,N-Dimethyltryptamine and 5-Methoxy-N,N-Dimethyltryptamine".Pharmacologist.17(2): 259.

[pmid21624387-3] Winter JC, Amorosi DJ, Rice KC, Cheng K, Yu AM (September 2011)."Stimulus control by 5-methoxy-N,N-dimethyltryptamine in wild-type and CYP2D6-humanized mice".Pharmacology, Biochemistry, and Behavior.99(3): 311–5.doi:10.1016/j.pbb.2011.05.015.PMC3129464.PMID 21624387.

[pmid8568822-4] Glennon RA, Hong SS, Bondarev M, Law H, Dukat M, Rakhi S, Power P, Fan E, Kinneau D, Kamboj R, Teitler M, Herrick-Davis K, Smith C (January 1996). "Binding of O-alkyl derivatives of serotonin at human 5-HT1D beta receptors".Journal of Medicinal Chemistry.39(1): 314–22.doi:10.1021/jm950498t.PMID 8568822.

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