Etymemazine

Etymemazine
Clinical data
Other names	Ethylisobutrazine
AHFS/Drugs.com	International Drug Names
ATC code	none;
Identifiers
	IUPAC name 3-(2-ethylphenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine;
CAS Number	523-54-6; HCl: 3737-33-5 ;
PubChem CID	71823;
ChemSpider	64847;
UNII	861J4K81C7; HCl: A7002E7T2Z ;
ChEMBL	ChEMBL1967567;
CompTox Dashboard (EPA)	DTXSID0046935 ;
Chemical and physical data
Formula	C20H26N2S
Molar mass	326.50 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C=C3)=CC2=C3SC1=CC=CC=C1N2CC(C)CN(C)C;
	InChI InChI=1S/C20H26N2S/c1-5-16-10-11-20-18(12-16)22(14-15(2)13-21(3)4)17-8-6-7-9-19(17)23-20/h6-12,15H,5,13-14H2,1-4H3; Key:USKHCLAXJXCWMO-UHFFFAOYSA-N;
	(verify)

Etymemazine is an antipsychotic, antihistamine and anticholinergic drug of the phenothiazine chemical class, structurally related to cyamemazine and methotrimeprazine.^[1]

Synthesis

Etymemazine can be synthesized by S_N2 alkylation of 2-ethylphenothiazine (1) with 1-dimethylamino-2-methyl-3-chloropropane (2) using sodamide as a base.^[2]^[3]

References

^ Milne GW (2002). "Etymemazine". Drugs: Synonyms and Properties (2nd ed.). Aldershot, Hampshire, England: Ashgate. p. 3945. ISBN 978-0-566-08491-1.
^ GB 789703 (1958 to Rhone Poulenc Sa).
^ Robert Michel Jacob, et al. U.S. patent 2,837,518 (1956 to Rhone Poulenc Sa)

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[1] Milne GW (2002). "Etymemazine". Drugs: Synonyms and Properties (2nd ed.). Aldershot, Hampshire, England: Ashgate. p. 3945. ISBN 978-0-566-08491-1.

[2] GB 789703 (1958 to Rhone Poulenc Sa).

[3] Robert Michel Jacob, et al. U.S. patent 2,837,518 (1956 to Rhone Poulenc Sa)

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