Dimenoxadol

Dimenoxadol (INN; also known as dimenoxadole (BAN) or dimenoxadole; brand name Estocin in Russia) is an opioid analgesic which is a benzilic acid derivative, closely related to benactyzine (an anticholinergic). Further, the structure is similar to methadone and related compounds like dextropropoxyphene.

Dimenoxadol

Clinical data
Other names	Dimenoxadol, Estocin
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs)[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I UN: Psychotropic Schedule I
Identifiers
IUPAC name 2-(dimethylamino)ethyl 2-ethoxy-2,2-diphenylacetate
CAS Number	509-78-4 Y
PubChem CID	17036
DrugBank	DB01461 Y
ChemSpider	16137 Y
UNII	4D65PBX0VK
KEGG	D12672 Y
ChEMBL	ChEMBL2104309
CompTox Dashboard (EPA)	DTXSID5057759
Chemical and physical data
Formula	C20H25NO3
Molar mass	327.424 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)OCCN(C)C
InChI InChI=1S/C20H25NO3/c1-4-24-20(17-11-7-5-8-12-17,18-13-9-6-10-14-18)19(22)23-16-15-21(2)3/h5-14H,4,15-16H2,1-3H3 Y Key:RHUWRJWFHUKVED-UHFFFAOYSA-N Y
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It was invented in Germany in the 1950s,^[2] and produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea.^[3][4][5]

In the United States it is a Schedule I Narcotic controlled substance with an ACSCN of 9617 and a 2013 annual aggregate manufacturing quota of zero.

Synthesis

The chemical synthesis has been reported:^[6] (according to:^[7]) Ref:^[8][9] Patent:^[10] Cmp#3:^[11]

• The reaction between 2-chloro-2,2-diphenylacetyl chloride [2902-98-9] (1) and Deanol [108-01-0] (2) gives [3042-75-9] (3). The intermediate haloalkane is then alkoxylated by refluxing in ethanol, completing the synthesis of Dimenoxadol (4).
• The 2-chloro-2,2-diphenylacetyl chloride is made by reacting benzilic acid with phosphorus pentachloride.^[12]