(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol hydrochloride

• ChemBase ID: 154285
• Molecular Formular: C16H26ClNO2
• Molecular Mass: 299.83614
• Monoisotopic Mass: 299.16520676
• SMILES: CN(C)C[C@H]1CCCC[C@@]1(c1cccc(c1)OC)O.Cl
• Canonical SMILES: COc1cccc(c1)[C@@]1(O)CCCC[C@@H]1CN(C)C.Cl
• InChI: InChI=1S/C16H25NO2.ClH/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;1H/t14-,16+;/m1./s1
• InChIKey: PPKXEPBICJTCRU-XMZRARIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol hydrochloride
• IUPAC Traditional name: tramadol hydrochloride
• Synonyms: (+)-Tramadol-d6 Hydrochloride; (1R,2R)-rel-2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride; cis-(+/-)-2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride; cis-Tramadol Hydrochloride; Amadol; Bellatram; CG 315; Contramal; Crispin; Omnidol; Poltram; Radol; Tadol; Ultram; Zumatran; Zydol; Tramadol Hydrochloride; (1R,2R)-2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride; (1R-cis)-2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride; (+)-trans-Tramadol Hydrochloride; E 382; (+)-Tramadol Hydrochloride; (±)-cis-2-(Dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol hydrochloride; Tramadol hydrochloride

Database IDs

• CAS Number: 148229-78-1; 36282-47-0; 1109217-84-6
• EC Number: 252-950-2
• MDL Number: MFCD00798507
• PubChem SID: 24724659; 162248424; 24866877
• PubChem CID: 63013

CALCULATED PROPERTIES

• Acid pKa: 13.7952175
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.8504328
• LogD (pH = 7.4): 0.6215551
• Log P: 2.4498615
• Molar Refractivity: 78.2692 cm^3
• Polarizability: 30.83849 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol; Water
• Apperance: White Solid; white to off-white solid
• Melting Point: 172-174°C; 178-181 °C; 180-184°C

Safety Information

• Storage Condition: -20°C Freezer; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-51/53
• Safety Statements: 61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H302-H411
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C16H25NO2 · HCl

DETAILS

Sigma Aldrich - UC456

Biochem/physiol Actions
Opioid analgesic; P450 substrate.

Sigma Aldrich - 42965

Biochem/physiol Actions
Opioid analgesic; P450 substrate.

Toronto Research Chemicals - T712515

An analgesic. Used in the treatment of urinary incontinence.

Toronto Research Chemicals - T712500

An analgesic.

Toronto Research Chemicals - T712517

Labelled (+)-Tramadol (T712515). An analgesic. Used in the treatment of urinary incontinence.

REFERENCES

• Dray, A., et al.: J. Pharmacol. Exp. Ther., 231, 254(1984)
• Raffa, R.B., et al.: J. Pharmacol. Exp. Ther., 267, 331 (1984)
• Dray, A., et al.: J. Pharmacol. Exp. Ther., 231, 254(1984)
• Raffa, R.B., et al.: J. Pharmacol. Exp. Ther., 267, 331 (1984)
• Raffa, R.B., et al.: J. Pharmacol. Exp. Ther., 267, 331 (1993)