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123154-38-1 molecular structure
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(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol

ChemBase ID: 78
Molecular Formular: C16H25NO2
Molecular Mass: 263.3752
Monoisotopic Mass: 263.18852905
SMILES and InChIs

SMILES:
O[C@]1([C@H](CCCC1)CN(C)C)c1cc(OC)ccc1
Canonical SMILES:
COc1cccc(c1)[C@@]1(O)CCCC[C@@H]1CN(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/t14-,16+/m1/s1
InChIKey:
TVYLLZQTGLZFBW-ZBFHGGJFSA-N

Cite this record

CBID:78 http://www.chembase.cn/molecule-78.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
IUPAC Traditional name
tramadol
Brand Name
Crispin
Ralivia ER
Ralivia Flashtab
Tramadol HCl BP/EP
Tramal
Ultram
Zydol
Tridural
Ultram ER
Synonyms
Tramadol HCl
Tramadol hydrochloride
Tramadolum [INN-Latin]
Tramodol Hcl
tramadol
Tramadol
(1R,2R)-2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol
(1R-cis)- 2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol
(+)-(R,R)-trans-Tramadol
(+)-trans-Tramadol
(+)-Tramadol
CAS Number
123154-38-1
27203-92-5
PubChem SID
160963541
46506256
PubChem CID
33741

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
T712510 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.7952175  H Acceptors
H Donor LogD (pH = 5.5) -0.8504328 
LogD (pH = 7.4) 0.6215551  Log P 2.4498615 
Molar Refractivity 78.2692 cm3 Polarizability 30.83849 Å3
Polar Surface Area 32.7 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.71  LOG S -2.55 
Solubility (Water) 7.50e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Dichloromethane expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Soluble in water. expand Show data source
Apperance
Light Yellow Oil expand Show data source
Hydrophobicity(logP)
2.4 expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC DrugBank DrugBank
Toronto Research Chemicals - T712510 external link
An analgesic. Used in the treatment of urinary incontinence.
DrugBank - DB00193 external link
Item Information
Drug Groups approved; investigational
Description A narcotic analgesic proposed for moderate to severe pain. It may be habituating. [PubChem]
Indication Indicated in the treatment of moderate to severe pain. Consider for those prone to constipation or respiratory depression. Tramadol is used to treat postoperative, dental, cancer, and acute musculosketetal pain and as an adjuvant to NSAID therapy in patients with osteoarthritis.
Pharmacology Tramadol, a centrally-acting analgesic, exists as a racemic mixture of the trans isomer, with important differences in binding, activity, and metabolism associated with the two enantiomers. Although Tramadol is a synthetic analog of codeine, it has a significantly lower affinity for opioid receptors than codeine.
Toxicity LD50=350mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation The major metabolic pathways appear to be N- and O- demethylation and glucuronidation or sulfation in the liver. One metabolite (O-desmethyltramadol, denoted M1) is pharmacologically active in animal models.
Absorption Racemic tramadol is rapidly and almost completely absorbed after oral administration. The mean absolute bioavailability of a 100 mg oral dose is approximately 75%.The mean peak plasma concentration of racemic tramadol and M1 occurs at two and three hours, respectively, after administration in healthy adults.
Half Life 23 +/- 10 minutes
Protein Binding 20%
Elimination Tramadol is eliminated primarily through metabolism by the liver and the metabolites are eliminated primarily by the kidneys. Tramadol and its metabolites are excreted primarily in the urine with observed plasma half-lives of 6.3 and 7.4 hours for tramadol and M1, respectively. Approximately 30% of the dose is excreted in the urine as unchanged drug, whereas 60% of the dose is excreted as metabolites.
Distribution * 2.6 L/kg [male 100 mg intravenous dose]
* 2.9 L/kg [female 100 mg intravenous dose]
Clearance * 5.9 mL/min/Kg [Healthy Adults, 100 mg qid, MD p.o]
* 8.5 mL/min/Kg [Healthy Adults, 100 mg SD p.o]
* 6.89 mL/min/Kg [Geriatric, (<75 yr), 50 mg SD p.o.]
* 4.23 mL/min/Kg [Hepatic Impaired, 50 mg SD p.o.]
* 4.23 mL/min/Kg [Renal Impaired, Clcr10-3mL/min, 100 mg SD i.v.]
* 3.73 mL/min/Kg [Renal Impaired, CLcr<5 mL/min, 100 mg SD i.v.]
* 6.4 mL/min/Kg [Male following a 100 mg IV dose]
* 5.7 mL/min/Kg [Female following a 100 mg IV dose]
References
Dayer P, Desmeules J, Collart L: [Pharmacology of tramadol] Drugs. 1997;53 Suppl 2:18-24. [Pubmed]
Harati Y, Gooch C, Swenson M, Edelman S, Greene D, Raskin P, Donofrio P, Cornblath D, Sachdeo R, Siu CO, Kamin M: Double-blind randomized trial of tramadol for the treatment of the pain of diabetic neuropathy. Neurology. 1998 Jun;50(6):1842-6. [Pubmed]
Harati Y, Gooch C, Swenson M, Edelman SV, Greene D, Raskin P, Donofrio P, Cornblath D, Olson WH, Kamin M: Maintenance of the long-term effectiveness of tramadol in treatment of the pain of diabetic neuropathy. J Diabetes Complications. 2000 Mar-Apr;14(2):65-70. [Pubmed]
Gobel H, Stadler T: [Treatment of post-herpes zoster pain with tramadol. Results of an open pilot study versus clomipramine with or without levomepromazine] Drugs. 1997;53 Suppl 2:34-9. [Pubmed]
Boureau F, Legallicier P, Kabir-Ahmadi M: Tramadol in post-herpetic neuralgia: a randomized, double-blind, placebo-controlled trial. Pain. 2003 Jul;104(1-2):323-31. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dray, A., et al.: J. Pharmacol. Exp. Ther., 231, 254(1984)
  • • Raffa, R.B., et al.: J. Pharmacol. Exp. Ther., 267, 331 (1984)
  • • Dayer P, Desmeules J, Collart L: [Pharmacology of tramadol] Drugs. 1997;53 Suppl 2:18-24. Pubmed
  • • Harati Y, Gooch C, Swenson M, Edelman S, Greene D, Raskin P, Donofrio P, Cornblath D, Sachdeo R, Siu CO, Kamin M: Double-blind randomized trial of tramadol for the treatment of the pain of diabetic neuropathy. Neurology. 1998 Jun;50(6):1842-6. Pubmed
  • • Harati Y, Gooch C, Swenson M, Edelman SV, Greene D, Raskin P, Donofrio P, Cornblath D, Olson WH, Kamin M: Maintenance of the long-term effectiveness of tramadol in treatment of the pain of diabetic neuropathy. J Diabetes Complications. 2000 Mar-Apr;14(2):65-70. Pubmed
  • • Gobel H, Stadler T: [Treatment of post-herpes zoster pain with tramadol. Results of an open pilot study versus clomipramine with or without levomepromazine] Drugs. 1997;53 Suppl 2:34-9. Pubmed
  • • Boureau F, Legallicier P, Kabir-Ahmadi M: Tramadol in post-herpetic neuralgia: a randomized, double-blind, placebo-controlled trial. Pain. 2003 Jul;104(1-2):323-31. Pubmed
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PATENTS

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