Tramadol |
Last updated: 21/05/2024 |
(Not known by any other names) |
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A synthetic codine analogue used in veterinary medicine which is usually formulated as the hydrochloride salt. | |
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Current | |
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1977, launched Germany; 1962, first synthesised | |
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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 | |
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Approved |
Chemical structure |
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Tramadol is a chiral molecule. The technical material is an isomeric mixture of both R- and S-stereoisomers | |
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C₁₆H₂₅NO₂ | |
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CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O | |
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CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O | |
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TVYLLZQTGLZFBW-ZBFHGGJFSA-N | |
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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 | |
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Common Name | Relationship | Link |
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tramadol hydrochloride | Variant |
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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27203-92-5 | |
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248-319-6 | |
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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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263.38 | |
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2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol | |
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(1R,2R)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexan-1-ol | |
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(+/-)-cis-(2-dimethylaminomethyl)-1-(3-methoxyphenyl)-cyclohexanol | |
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Formulations |
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Available as the hydrochloride salt as tablets for oral administration and as solutions for injection |
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39.5 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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180 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) as the HCl salt3 = Unverified data of known source |
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2.24 X 1001 | Calculated | - | |||||||
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1.35 | 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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9.41 | F3 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 ) 3 = Unverified data of known source |
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Degradation |
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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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Soil adsorption and mobility |
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Fate indices |
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Known soil and groundwater metabolites |
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Other known metabolites |
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O-desmethyltramadol | - | Human liver | - | ||||
N-desmethyltramadol | - | Human liver | - | ||||
O-desmethyl-tramado glucuronide | - | Human liver | - | ||||
N,O-didesmethyltramadol | - | Human liver | - | ||||
N,N-didesmethyltramadol | - | Human liver | - | ||||
N,N,O-tridesmethyl-tramadol | - | Human liver | - | ||||
N,N,O-tridesmethyl-tramadol | - | Human liverl | - |
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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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Aquatic ecotoxicology |
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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 |
Moderate | ||||||||
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Intraperitoneal LD₅₀ = 150 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Subcutaneous LD₅₀ = 286 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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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 |
Handling issues |
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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 | ||
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Record last updated: | 21/05/2024 |
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 |