tramadol   Click here for help

GtoPdb Ligand ID: 8286

Synonyms: (1RS,2RS)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-cyclo-hexanol | Maxitram® | Tilodol® | Tramacet®
Approved drug
tramadol is an approved drug (FDA (1995), UK (2003))
Compound class: Synthetic organic
Comment: Tramadol is a narcotic-like analgesic.
The marketed formulation of tramadol is a racemic mixture of enantiomers, including PubChem CIDs 33741 and 667511 (and others). We represent the non-isomeric molecule to represent the mixture. The clinically administered form is tramadol hydrochloride.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 32.7
Molecular weight 263.19
XLogP 2.43
No. Lipinski's rules broken 0
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Canonical SMILES COc1cccc(c1)C1(O)CCCCC1CN(C)C
Isomeric SMILES COc1cccc(c1)C1(O)CCCCC1CN(C)C
InChI InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3
1. Hennies HH, Friderichs E, Schneider J. (1988)
Receptor binding, analgesic and antitussive potency of tramadol and other selected opioids.
Arzneimittelforschung, 38 (7): 877-80. [PMID:2849950]
2. Leppert W. (2009)
Tramadol as an analgesic for mild to moderate cancer pain.
Pharmacol Rep, 61 (6): 978-92. [PMID:20081232]
3. Raffa RB, Friderichs E, Reimann W, Shank RP, Codd EE, Vaught JL. (1992)
Opioid and nonopioid components independently contribute to the mechanism of action of tramadol, an 'atypical' opioid analgesic.
J Pharmacol Exp Ther, 260 (1): 275-85. [PMID:1309873]
4. Wentland MP, Lou R, Lu Q, Bu Y, Denhardt C, Jin J, Ganorkar R, VanAlstine MA, Guo C, Cohen DJ et al.. (2009)
Syntheses of novel high affinity ligands for opioid receptors.
Bioorg Med Chem Lett, 19 (8): 2289-94. [PMID:19282177]
5. Wentland MP, Lou R, Lu Q, Bu Y, VanAlstine MA, Cohen DJ, Bidlack JM. (2009)
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
Bioorg Med Chem Lett, 19 (1): 203-8. [PMID:19027293]