Tilidine
Basic information
- CAS
20380-58-9- Standard SMILES
CCOC(=O)[C@]1(c2ccccc2)CCC=C[C@H]1N(C)C- InChIKey
WDEFBBTXULIOBB-WBVHZDCISA-N- Molecular formula
- C17H23NO2
- Average molar mass
- 273.37 g/mol
- Monoisotopic mass
- 273.17287898
Overview
Dextilidine is an ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has S configuration at the carbon bearing the phenyl group and R configuration at the carbon bearing the dimethylamino group. The opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and its enantiomer, ent-dextilidine. A prodrug, tilidine is converted by the liver to the active analgesic, nortilidine; virtually all of the opioid activity resides in the (1S,2R) isomer (i.e. the isomer derived from dextilidine). It has a role as an opioid analgesic and a prodrug. It is an enantiomer of an ent-dextilidine.
Names & identifiers
- Preferred name
- Tilidine
- IUPAC
- ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
- English name
- ethyl trans-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
- Molecular formula
- C17H23NO2
- Molecular weight
- 273.37
Names & synonyms
TilidateTILIDINEtrans-Tilidinedl-trans-Tilidine51931-66-920380-58-9ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylateGY33N31E9YIDS-NT-003DTXSID90236713-Cyclohexene-1-carboxylic acid, 2-(dimethylamino)-1-phenyl-, ethyl ester, (1R,2S)-rel-Go 1261
Show more names
Dea no. 9750Tilidate [ban]Einecs 257-522-9Tilidine for system suitabilityTilidine 0.1 mg/ml in Acetonitrileethyl trans-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylateEthyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylate3-Cyclohexene-1-carboxylic acid, 2-(dimethylamino)-1-phenyl-, ethyl ester, trans-
Godecke, TilidinRefChem:898119DTXCID003671CHEBI:77823Go1261DTXSID401347825243-774-7257-522-9
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 358
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Narcotic Analgesics
DEA Schedule I Controlled Substance -> Opiates
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Physicochemical properties
- Boiling point
- 96 °C · 96 °C(Press: 0.01 Torr)
- Density
- 1.06 · 1.06±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- pka
- 8.26 · 8.26±0.40(Predicted)
- InChI
- 1S/C17H23NO2/c1-4-20-16(19)17(14-10-6-5-7-11-14)13-9-8-12-15(17)18(2)3/h5-8,10-12,15H,4,9,13H2,1-3H3/t15-,17/m1/s1
- InChIKey
- WDEFBBTXULIOBB-LDCVWXEPSA-N
- SMILES
- N([C@H]1C(CCC=C1)(c2ccccc2)C(=O)OCC)(C)C
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 33 N31E9Y · GY33N31E9Y
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
DEA schedule I controlled substance
REACH registered substance: Ethyl trans-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate (EC: 257-522-9)
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H332-H302-H373-H312-H334
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralResp. Sens. 1STOT RE 2
- Precautionary statements
- P260-P314-P501-P280-P302+P352-P312-P322-P363-P501-P261-P285-P304+P341-P342+P311-P501-P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological Classification
Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >25000
Applications
UsesTilidine is an opioid used primarily as a painkiller it inhibits the enzyme adenylyl cyclase.
Additional notes
DefinitionChEBI: Dextilidine is an ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has S configuration at the carbon bearing the phenyl group and R configuration at the carbon bearing the dimethylamino group. The opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and its enantiomer, ent-dextilidine. A prodrug, tilidine is converted by the liver to the active analgesic, nortilidine; virtually all of the opioid activity resides in the (1S,2R) isomer (i.e. the isomer derived from dextilidine). It has a role as an opioid analgesic and a prodrug. It is an enantiomer of an ent-dextilidine.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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