Basic information
- CAS
148229-78-1- Standard SMILES
COc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1.Cl- InChIKey
PPKXEPBICJTCRU-XMZRARIVSA-N- Molecular formula
- C16H26ClNO2
- Average molar mass
- 299.83 g/mol
- Monoisotopic mass
- 299.1652068
Overview
(R,R)-tramadol hydrochloride is a hydrochloride resulting from the reaction of (R,R)-tramadol with 1 molar equivalent of hydrogen chloride; the (R,R)-enantiomer of the racemic opioid analgesic tramadol hydrochloride, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. It has a role as an opioid analgesic, an adrenergic uptake inhibitor, a serotonergic antagonist, a muscarinic antagonist, a nicotinic antagonist, a serotonin uptake inhibitor, an antitussive, a mu-opioid receptor agonist, a kappa-opioid receptor agonist, a NMDA receptor antagonist, a delta-opioid receptor agonist and a capsaicin receptor antagonist. It contains a (R,R)-tramadol(1+). It is an enantiomer of a (S,S)-tramadol hydrochloride.
Names & identifiers
- Preferred name
- Tramadol Hydrochloride
- IUPAC
- cis-(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol;hydrochloride
- English name
- (+)-TRAMADOL, HYDROCHLORIDE
- Molecular formula
- C16H25NO2.ClH
- Molecular weight
- 299.84
Names & synonyms
tramadol hydrochloride36282-47-0Tramadol HClTradonalAmadolMabronZydolConZipSynaprynRyzoltUltram ERRybix ODT
Show more names
E 382DL-Tramadolhydrochlorid(+)-(1R,2R)-TRAMADOL HCL(+)-Tramadol hydrochloride(+)-trans-Tramadol Hydrochloride(+)-(1R,2R)-Tramadol hydrochloride(+)-2-[(DIMETHYLAMINO)METHYL]-1-(3-METHOXYPHENYL)CYCLOHEXANOL, HYDROCHLORIDE(1R,2R)-2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride(1R-cis)-2-[(DiMethylaMino)Methyl]-1-(3-Methoxyphenyl)cyclohexanol Hydrochloride(+)-Tramadol HydrochlorideQ: What is (+)-Tramadol Hydrochloride Q: What is the CAS Number of (+)-Tramadol Hydrochloride Q: What is the storage condition of (+)-Tramadol Hydrochloride Q: What are the applications of (+)-Tramadol Hydrochloride
ZamudolZertaneDTXSID7023691QDOLO9N7R477WCKTramadol hydrochloride civU-26,225ADTXCID60809617
Properties
Computed structural properties
- Topological polar surface area
- 32.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 282
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesics, Opioid; Narcotics
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Collision Cross Section160.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 172 · 172-174°C
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- White to Off-White
- Stability
- Hygroscopic
- CAS DataBase Reference
- 148229 · 148229-78-1
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
Danger
H301 (57.8%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P301+P317, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 135 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301 (41.5%): Toxic if swallowed [Danger Acute toxicity, oral]
Hazard information
Regulatory Informationcis-Tramadol hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Acute Tox. 3 (57.8%)
Acute Tox. 3 (41.5%)
Toxicology
Treatment
In treating an overdose, primary attention should be given to maintaining adequate ventilation along with general supportive treatment. While naloxone will reverse some, but not all, symptoms caused by overdosage with ULTRAM, the risk of seizures is also increased with naloxone administration. (L1712)
Health Effects
Serious potential consequences of overdosage are respiratory depression, lethargy, coma, seizure, cardiac arrest and death. The respiratory depressant effects include carbon dioxide retention and secondary elevation of cerebrospinal fluid pressure, and may be markedly exaggerated in these patients (RxList, A308). Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Hepatic. 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. CYP3A4 and CYP2B6 facilitates the biotransformation of tramadol to N-desmethyl-tramadol. CYP2D6 facilitates the biotransformation of tramadol to O-desmethyl-tramadol. 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. Tramadol undergoes hepatic metabolism via the cytochrome P450 isozyme CYP2D6, being O- and N-demethylated to five different metabolites. Of these, M1 (O-Desmethyltramadol) is the most significant since it has 200 times the affinity of (+)-tramadol, and furthermore has an elimination half-life of nine hours, compared with six hours for tramadol itself. In the 6% of the population that have slow CYP2D6 activity, there is therefore a slightly reduced analgesic effect. Phase II hepatic metabolism renders the metabolites water-soluble, which are excreted by the kidneys. Thus, reduced doses may be used in renal and hepatic impairment (A308, L1160). Route of Elimination: Tramadol is eliminated primarily through metabolism by the liver and the metabolites are excreted primarily by the kidneys. Approximately 30% of the dose is excreted in the urine as unchanged drug, whereas 60% of the dose is excreted as metabolites. Half Life: 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.
FDA Pharmacological Classification
TRAMADOL HCL
Full Opioid Agonists [MoA]; Opioid Agonist [EPC]
TRAMADOL HYDROCHLORIDE
Opioid Agonist [EPC]; Full Opioid Agonists [MoA]
TRAMADOL HCL ER
Opioid Agonist [EPC]; Full Opioid Agonists [MoA]
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.
Related reactions
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Compound notes
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