Nortilidine

Nortilidine
Identifiers
	IUPAC name ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate;
CAS Number	38677-94-0;
PubChem CID	162321;
ChemSpider	142535;
UNII	7145G6817J;
ChEBI	CHEBI:77839 ;
ChEMBL	ChEMBL1614654;
CompTox Dashboard (EPA)	DTXSID10191256 ;
Chemical and physical data
Formula	C16H21NO2
Molar mass	259.349 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2;
	InChI InChI=1S/C16H21NO2/c1-3-19-15(18)16(13-9-5-4-6-10-13)12-8-7-11-14(16)17-2/h4-7,9-11,14,17H,3,8,12H2,1-2H3/t14-,16+/m0/s1; Key:PDJZPNKVLDWEKI-GOEBONIOSA-N;

Nortilidine^[1] is the major active metabolite of tilidine. It is formed from tilidine by demethylation in the liver. The racemate has opioid analgesic effects roughly equivalent in potency to that of morphine.^[2] The (1R,2S) isomer has NMDA antagonist activity. The drug also acts as a dopamine reuptake inhibitor.^[3] The reversed-ester of nortilidine is also known, as is the corresponding analogue with the cyclohexene ring replaced by cyclopentane,^[4] which have almost identical properties to nortilidine.^[5]

Use

Nortilidine has been sold as a designer drug, first being identified in Poland in May 2020.^[6]^[7]

References

^ US 3792080, "Process for Substituted Cyclohexenes its Products"
^ Hajda JP, Jähnchen E, Oie S, Trenk D (November 2002). "Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine". Journal of Clinical Pharmacology. 42 (11): 1257–61. doi:10.1177/009127002762491352. PMID 12412825. S2CID 12390653.
^ Schifano F, Orsolini L, Duccio Papanti G, Corkery JM (February 2015). "Novel psychoactive substances of interest for psychiatry". World Psychiatry. 14 (1): 15–26. doi:10.1002/wps.20174. PMC 4329884. PMID 25655145.
^ US 4291059, "Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic"
^ Personal Communication with Derek P. Reynolds
^ "EU Early Warning System Situation Report. Situation report 2". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 10 August 2020. {{cite web}}: Missing or empty |url= (help)
^ Catalani V, Arillotta D, Corkery JM, Guirguis A, Vento A, Schifano F (2020). "Identifying New/Emerging Psychoactive Substances at the Time of COVID-19; A Web-Based Approach". Frontiers in Psychiatry. 11: 632405. doi:10.3389/fpsyt.2020.632405. PMC 7900492. PMID 33633599.

External links

Media related to Nortilidine at Wikimedia Commons

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[1] US 3792080, "Process for Substituted Cyclohexenes its Products"

[pmid12412825-2] Hajda JP, Jähnchen E, Oie S, Trenk D (November 2002). "Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine". Journal of Clinical Pharmacology. 42 (11): 1257–61. doi:10.1177/009127002762491352. PMID 12412825. S2CID 12390653.

[SchifanoOrsolini2015-3] Schifano F, Orsolini L, Duccio Papanti G, Corkery JM (February 2015). "Novel psychoactive substances of interest for psychiatry". World Psychiatry. 14 (1): 15–26. doi:10.1002/wps.20174. PMC 4329884. PMID 25655145.

[4] US 4291059, "Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic"

[5] Personal Communication with Derek P. Reynolds

[6] "EU Early Warning System Situation Report. Situation report 2". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 10 August 2020. {{cite web}}: Missing or empty |url= (help)

[pmid33633599-7] Catalani V, Arillotta D, Corkery JM, Guirguis A, Vento A, Schifano F (2020). "Identifying New/Emerging Psychoactive Substances at the Time of COVID-19; A Web-Based Approach". Frontiers in Psychiatry. 11: 632405. doi:10.3389/fpsyt.2020.632405. PMC 7900492. PMID 33633599.

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Nortilidine

Contents

Use

See also

References

External links

Identifiers

IUPAC name ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
CAS Number	38677-94-0
PubChem CID	162321
ChemSpider	142535
UNII	7145G6817J
ChEBI	CHEBI:77839^Y
ChEMBL	ChEMBL1614654
CompTox Dashboard (EPA)	DTXSID10191256
Chemical and physical data
Formula	C₁₆H₂₁NO₂
Molar mass	259.349 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2
InChI InChI=1S/C16H21NO2/c1-3-19-15(18)16(13-9-5-4-6-10-13)12-8-7-11-14(16)17-2/h4-7,9-11,14,17H,3,8,12H2,1-2H3/t14-,16+/m0/s1 Key:PDJZPNKVLDWEKI-GOEBONIOSA-N