Benanserin

Benanserin

Clinical data
Other names	Benanserine; MC-4788; Sq-4788; Benzyl antiserotonin; Benzylantiserotonin; BAS; Serotonin benzyl analogue; Wooley's antiserotonin; 1-Benzyl-2-methyl-5-methoxytryptamine
Routes of administration	Oral, intravenous injection[1]
Drug class	Serotonin receptor antagonist; Tranquilizer
Identifiers
IUPAC name 2-(1-benzyl-5-methoxy-2-methylindol-3-yl)ethanamine
CAS Number	441-91-8
PubChem CID	9925
ChemSpider	9537
UNII	9G5WZ7RO2D
ChEMBL	ChEMBL1740857
CompTox Dashboard (EPA)	DTXSID40196037
Chemical and physical data
Formula	C19H22N2O
Molar mass	294.398 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C2=C(N1CC3=CC=CC=C3)C=CC(=C2)OC)CCN
InChI InChI=1S/C19H22N2O/c1-14-17(10-11-20)18-12-16(22-2)8-9-19(18)21(14)13-15-6-4-3-5-7-15/h3-9,12H,10-11,13,20H2,1-2H3 Key:RPSOLZRELOLSFM-UHFFFAOYSA-N

Benanserin, also known as benzyl antiserotonin (BAS), by its developmental code name MC-4788 or Sq-4788, and by its chemical name 1-benzyl-2-methyl-5-methoxytryptamine, is a serotonin receptor antagonist and described tranquilizer of the tryptamine and 5-methoxytryptamine families.^[2][1][3][4] It is the derivative of 5-methoxytryptamine with a benzyl group at the 1 position and a methyl group at the 2 position.^[2][3] The drug is said to be active in humans at a dose of 10 to 35 mg orally or intravenously.^[1] In contrast to certain other serotonin receptor antagonists like chlorpromazine, benanserin does not antagonize the subjective effects of the serotonergic psychedelic LSD.^[4] It was first described in the scientific literature by at least 1955 and was one of the first serotonin antagonists.^[2][5]

1. ^ ^{a b c} Usdin E, Efron DH (1972). Psychotropic Drugs and Related Compounds. National Institute of Mental Health. Retrieved 28 June 2025.
2. ^ ^{a b c} Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3. Retrieved 28 June 2025.
3. ^ ^{a b} Negwer M (2001). Organic-chemical Drugs and Their Synonyms: An International Survey. Wiley-VCH. p. 2442. ISBN 978-3-527-30247-5. Retrieved 28 June 2025.
4. ^ ^{a b} Martin WR, Sloan JW (1977). "Pharmacology and Classification of LSD-like Hallucinogens". Drug Addiction II: Amphetamine, Psychotogen, and Marihuana Dependence. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 305–368. doi:10.1007/978-3-642-66709-1_3. ISBN 978-3-642-66711-4.
5. ^ Shaw E (1955). "The Synthesis of Tryptamines Related to Serotonin". Journal of the American Chemical Society. 77 (16): 4319–4324. Bibcode:1955JAChS..77.4319S. doi:10.1021/ja01621a042. ISSN 0002-7863. Retrieved 28 June 2025.

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