1-(2-Chloro-N-methylbenzimidoyl)cyclopentanol

1-(2-Chloro-N-methylbenzimidoyl)cyclopentanol, sometimes misleadingly referred to as hydroxylimine hydrochloride, is a chemical compound which is the final intermediate in the synthesis of ketamine, an anaesthetic drug which is also subject to recreational abuse. This chemical intermediate is not active as a drug in its own right, and is legal in most countries, but is readily converted into ketamine by dissolving it in a suitable high-boiling point solvent and heating, with no other chemicals required.^[1][2] This has made it subject to illicit trade as a drug precursor, and it has sometimes been seized by law enforcement agencies in significant quantities, leading to it being specifically banned as a controlled drug precursor in some jurisdictions such as Taiwan.^[3][4]

1-(2-Chloro-N-methylbenzimidoyl)cyclopentanol

Identifiers
IUPAC name 1-[C-(2-chlorophenyl)-N-methylcarbonimidoyl]cyclopentan-1-ol
CAS Number	6740-87-0 hydrochloride: 90717-16-1
PubChem CID	13086940
ChemSpider	26551984
UNII	HGI99H315N
CompTox Dashboard (EPA)	DTXSID60217758
ECHA InfoCard	100.169.732
Chemical and physical data
Formula	C13H16ClNO
Molar mass	237.73 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN=C(C1=CC=CC=C1Cl)C2(CCCC2)O
InChI InChI=1S/C13H16ClNO/c1-15-12(13(16)8-4-5-9-13)10-6-2-3-7-11(10)14/h2-3,6-7,16H,4-5,8-9H2,1H3 Key:FJGPXUPMNZOTLX-UHFFFAOYSA-N

See also

• 1-Boc-4-AP
• 1,6-Dioxecane-2,7-dione
• Alprazolam triazolobenzophenone

References

1. US patent 3254124, Stevens CL, "Aminoketones and methods for their production", issued 1966-05-31, assigned to Parke Davis & Co.
2. Dimitrov I, Denny WA, Jose J (2018). "Syntheses of Ketamine and Related Analogues: A Mini Review". Synthesis. 50 (21): 4201–4215. doi:10.1055/s-0037-1609935. S2CID 105931970.
3. "200 kg of ketamine precursor seized at Taoyuan Airport". Taiwan News. 1 January 2009.
4. "Taiwan catches 2 tons of drugs hidden inside machinery from China". Taiwan News. 31 March 2018.