Tramadol hydrochloride |
![]() Last updated: 14/09/2025 |
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(Also known as: tramadol HCl) |
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A synthetic codine analogue used in veterinary medicine | |
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Used to control acute and chronic pain of moderate to severe intensity | |
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Dogs |
Approval status |
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Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Tramadol hydrochloride exhibits chiral isomerism, as it contains two stereocentres within its cyclohexanol ring structure. This gives rise to four possible stereoisomers, but the drug is typically formulated as a racemic mixture of the two enantiomers: (1R,2R)-tramadol and (1S,2S)-tramadol. | |
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C₁₆H₂₆ClNO₂ | |
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CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O.Cl | |
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CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O.Cl | |
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PPKXEPBICJTCRU-XMZRARIVSA-N | |
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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 | |
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Yes |
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Common Name | Relationship | Link |
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tramadol hydrochloride | - | ![]() |
General status |
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Medicinal drug: Analgesic | |
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Opoid | |
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Synthetic | |
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Multiple activity routes | |
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[µ-opioid receptor, Agonist], [Sodium-dependent noradrenaline transporter, Inhibitor], [Sodium-dependent serotonin transporter, Inhibitor], [5-hydroxytryptamine receptor 2C, Antagonist], [Kappa-type opioid receptor, Agonist], [Delta-type opioid receptor, Agonist] | |
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36282-47-0 | |
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252-950-2 | |
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63013 | |
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Nervous system: Other opioids | |
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QN02AX02 | |
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UK: Class C, Schedule 3 | |
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299.83 | |
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(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol;hydrochloride | |
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Commercial |
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Current | |||
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1977, launched Germany; 1962, first synthesised | |||
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Available as tablets for oral administration and as solutions for injection | |||
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The production of tramadol hydrochloride typically begins with the synthesis of its key intermediate, 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexanol, which is formed via a Grignard reaction between m-methoxyphenyl magnesium bromide and 2-dimethylaminomethylcyclohexanone in a solvent such as 2-methyltetrahydrofuran, chosen for its low environmental impact. The resulting crude base is then purified and subjected to salification by reacting with hydrochloric acid in an alcoholic solution, forming the hydrochloride salt of tramadol. This step is often carried out in the presence of a small amount of water to catalyse the reaction. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Fate indices |
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Known metabolites |
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Terrestrial ecotoxicology |
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350 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
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> 154.5 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Daphnia magna4 = Verified data |
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General |
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350 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
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Extensively metabolised in the liver (0% eliminated in the urine, 10% in faeces) | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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Health issues |
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CNS depressant May depress respiratory function Some incidences of adverse reactions recorded including headache, diarrhoea, vomiting & cardiovascular irregularities |
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Will emit toxic fumes when heated to decomposition | |||
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Not listed (Not listed) | |||
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tramadol hydrochloride | ||
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Record last updated: | 14/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |