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    Tramadol Hydrochloride
    Also known as: 36282-47-0, Contramal, (+)-tramadol hydrochloride, Tradonal, 148229-78-1, Cis-tramadol hydrochloride
    Molecular Formula
    C16H26ClNO2
    Molecular Weight
    299.83  g/mol
    InChI Key
    PPKXEPBICJTCRU-XMZRARIVSA-N
    FDA UNII
    9N7R477WCK
    A narcotic analgesic proposed for severe pain. It may be habituating.
    1 2D Structure

    Tramadol Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol;hydrochloride
    2.1.2 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
    2.1.3 InChI Key
    PPKXEPBICJTCRU-XMZRARIVSA-N
    2.1.4 Canonical SMILES
    CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O.Cl
    2.1.5 Isomeric SMILES
    CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    9N7R477WCK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Adolonta

    2. Amadol

    3. Biodalgic

    4. Biokanol

    5. Contramal

    6. Jutadol

    7. K 315

    8. K-315

    9. K315

    10. Mtw Tramadol

    11. Mtw-tramadol

    12. Mtwtramadol

    13. Nobligan

    14. Prontofort

    15. Ranitidin 1a Pharma

    16. Takadol

    17. Theradol

    18. Tiral

    19. Topalgic

    20. Tradol

    21. Tradol Puren

    22. Tradol-puren

    23. Tradolpuren

    24. Tradonal

    25. Tralgiol

    26. Trama 1a Pharma

    27. Trama Abz

    28. Trama Dorsch

    29. Trama Kd

    30. Trama-dorsch

    31. Tramabeta

    32. Tramadin

    33. Tramadoc

    34. Tramadol

    35. Tramadol 1a

    36. Tramadol Acis

    37. Tramadol Al

    38. Tramadol Asta Medica

    39. Tramadol Basics

    40. Tramadol Bayvit

    41. Tramadol Bexal

    42. Tramadol Cinfa

    43. Tramadol Dolgit

    44. Tramadol Edigen

    45. Tramadol Hameln

    46. Tramadol Heumann

    47. Tramadol Kern

    48. Tramadol Lichtenstein

    49. Tramadol Lindo

    50. Tramadol Mabo

    51. Tramadol Normon

    52. Tramadol Pb

    53. Tramadol Ratiopharm

    54. Tramadol Stada

    55. Tramadol-dolgit

    56. Tramadol-hameln

    57. Tramadol-ratiopharm

    58. Tramadoldolgit

    59. Tramadolhameln

    60. Tramadolor

    61. Tramadolratiopharm

    62. Tramadorsch

    63. Tramadura

    64. Tramagetic

    65. Tramagit

    66. Tramake

    67. Tramal

    68. Tramex

    69. Tramundin

    70. Trasedal

    71. Ultram

    72. Xymel 50

    73. Zamudol

    74. Zumalgic

    75. Zydol

    76. Zytram

    2.3.2 Depositor-Supplied Synonyms

    1. 36282-47-0

    2. Contramal

    3. (+)-tramadol Hydrochloride

    4. Tradonal

    5. 148229-78-1

    6. Cis-tramadol Hydrochloride

    7. Tramadol Hcl

    8. Amadol

    9. Zydol

    10. Conzip

    11. 22204-88-2

    12. Tramal

    13. Zydol Hydrochloride

    14. Crispin

    15. Ryzolt

    16. Cg-315e

    17. 9n7r477wck

    18. 194602-08-9

    19. Bellatram

    20. Omnidol

    21. Zumatran

    22. Chebi:75733

    23. Radol

    24. Tadol

    25. (1r,2r)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol;hydrochloride

    26. Melanate

    27. Poltram

    28. Tramadex

    29. Tramagetic

    30. Tramazac

    31. U-26225a

    32. Dolana

    33. Mabron

    34. Trabar

    35. Tramed

    36. Tramol

    37. Tridol

    38. U-26,225a

    39. Tradol-puren

    40. (1r,2r)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride

    41. Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, Hydrochloride, (1r,2r)-rel-

    42. Zamudol

    43. Zertane

    44. Tramadolhydrochloride

    45. Adolanta

    46. Cemadol

    47. Synapryn

    48. Tridural

    49. Rybix

    50. Viotra

    51. Tramal Retard

    52. Ira-tramadol

    53. Ultram Er

    54. Cyclohexanol, 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-,hydrochloride, (1r,2r)-rel-

    55. Rybix Odt

    56. Cg 315

    57. Smr000449308

    58. Tramadol Hydrochloride Civ

    59. Tramadol Related Compound A

    60. Zydol Xl 150

    61. Einecs 252-950-2

    62. Unii-9n7r477wck

    63. Tramundin

    64. Cg-315

    65. Nih-10969

    66. Nsc-759105

    67. (1r,2r)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol Hydrochloride

    68. (1r,2r)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol Hydrochloride

    69. Nih 10969

    70. Ultram (tn)

    71. Qdolo

    72. Tramadole Hydrochloride

    73. Tramadol/hcl

    74. Tramadol Hydrochloride [usan:usp:jan]

    75. (+-)-cis-2-((dimethylamino)methyl)-1-(m-methoxyphenyl)cyclohexanol Hydrochloride

    76. Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, Hydrochloride, Cis-

    77. Schembl41748

    78. (r,r)-tramadol Hydrochloride

    79. 53611-16-8

    80. Mls000758218

    81. Mls001424208

    82. Chembl1200336

    83. Dtxsid7023691

    84. Hy-b0582a

    85. Tramadol Hydrochloride, Ep Grade

    86. Dtxsid60933340

    87. (1rs,2sr)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride

    88. Tramadol Hydrochloride [mi]

    89. 3,3,4,4-terephthaloydiphthalicacid

    90. Tramadol Hydrochloride (jp17/usp)

    91. Tramadol Hydrochloride [jan]

    92. Ac-796

    93. Mfcd00798507

    94. Tramadol Hydrochloride [hsdb]

    95. Tramadol Hydrochloride [usan]

    96. Tramadol Hydrochloride [vandf]

    97. (+)-(1r,2r)-tramadol Hydrochloride

    98. Akos015907739

    99. Tramadol Hydrochloride [mart.]

    100. Ccg-101135

    101. Ks-1124

    102. Nc00385

    103. Nsc 759105

    104. Tramadol Hydrochloride [who-dd]

    105. (+-)-cis-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol Hydrochloride

    106. Bt162445

    107. Tramadol Hydrochloride [orange Book]

    108. Tramadol Hydrochloride Civ [usp-rs]

    109. Tramadol Hydrochloride, >=99.0% (hplc)

    110. Tramadol Hydrochloride [ep Monograph]

    111. Tramadol Hydrochloride [usp Monograph]

    112. D01355

    113. Tramadol Hydrochloride, >=98% (hplc), Solid

    114. Ultracet Component Tramadol Hydrochloride

    115. 204t882

    116. Sr-01000759320

    117. Tramadol Hydrochloride Component Of Ultracet

    118. Q-201847

    119. Sr-01000759320-5

    120. Q27145507

    121. Tramadol Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

    122. (+)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Hydrochloride

    123. Tramadol Hydrochloride, British Pharmacopoeia (bp) Reference Standard

    124. Tramadol Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    125. Tramadol Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    126. (+/-)-cis-2-((dimethylamino)methyl)-1-(m-methoxyphenyl)cyclohexanol Hydrochloride

    127. (1r,2r)-2-(dimethylaminomethyl)-1-(3-methoxyphenyl)-cyclohexanol Hydrochloride

    128. [(1r,2r)-2-hydroxy-2-(3-methoxyphenyl)cyclohexyl]-n,n-dimethylmethanaminium Chloride

    129. 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol--hydrogen Chloride (1/1)

    130. Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, Hydrochloride, Cis-(+-)-

    131. Cis-tramadol Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

    132. Cyclohexanol, 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-, (1r,2r)-, Hydrochloride (1:1)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 299.83 g/mol
    Molecular Formula C16H26ClNO2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass299.1652068 g/mol
    Monoisotopic Mass299.1652068 g/mol
    Topological Polar Surface Area32.7 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity282
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameConzip
    PubMed HealthTramadol (By mouth)
    Drug ClassesAnalgesic
    Drug LabelConZip (tramadol hydrochloride) capsules is a centrally acting synthetic analgesic in an extended-release oral formulation. The chemical name for tramadol hydrochloride is ()cis-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl) cyclohexanol hydrochl...
    Active IngredientTramadol hydrochloride
    Dosage FormCapsule, extended release
    RouteOral
    Strength300mg; 200mg; 100mg; 150mg
    Market StatusPrescription
    CompanyCipher Pharms

    2 of 6  
    Drug NameTramadol hydrochloride
    PubMed HealthTramadol (By mouth)
    Drug ClassesAnalgesic
    Drug LabelTramadol hydrochloride is a centrally acting synthetic analgesic in an extended-release formulation. The chemical name is ()cis-2-[(dimethylamino) methyl]-1-(3-methoxyphenyl) cyclohexanol hydrochloride. Its structural formula is: Figure 1The molecu...
    Active IngredientTramadol hydrochloride
    Dosage FormTablet, extended release; Tablet
    RouteOral
    Strength200mg; 300mg; 100mg; 50mg
    Market StatusPrescription
    CompanyAnchen Pharms; Amneal Pharms; Mylan Pharms; Teva; Apotex; Accord Hlthcare; Aurobindo Pharma; Cspc Ouyi Pharm; Sun Pharm Inds; Lupin; Mallinckrodt; Allied Pharma; Northstar Hlthcare; Sun Pharma Global; Par Pharm; Actavis Elizabeth; Ipca Labs; Mutual Pharm;

    3 of 6  
    Drug NameUltram er
    Drug LabelULTRAMER (tramadol hydrochloride) is a centrally acting synthetic analgesic in an extended-release formulation. The chemical name is (cis-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl) cyclohexanol hydrochloride. Its structural formula is:Figure 1The...
    Active IngredientTramadol hydrochloride
    Dosage FormTablet, extended release
    RouteOral
    Strength200mg; 300mg; 100mg
    Market StatusPrescription
    CompanyValeant Intl

    4 of 6  
    Drug NameConzip
    PubMed HealthTramadol (By mouth)
    Drug ClassesAnalgesic
    Drug LabelConZip (tramadol hydrochloride) capsules is a centrally acting synthetic analgesic in an extended-release oral formulation. The chemical name for tramadol hydrochloride is ()cis-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl) cyclohexanol hydrochl...
    Active IngredientTramadol hydrochloride
    Dosage FormCapsule, extended release
    RouteOral
    Strength300mg; 200mg; 100mg; 150mg
    Market StatusPrescription
    CompanyCipher Pharms

    5 of 6  
    Drug NameTramadol hydrochloride
    PubMed HealthTramadol (By mouth)
    Drug ClassesAnalgesic
    Drug LabelTramadol hydrochloride is a centrally acting synthetic analgesic in an extended-release formulation. The chemical name is ()cis-2-[(dimethylamino) methyl]-1-(3-methoxyphenyl) cyclohexanol hydrochloride. Its structural formula is: Figure 1The molecu...
    Active IngredientTramadol hydrochloride
    Dosage FormTablet, extended release; Tablet
    RouteOral
    Strength200mg; 300mg; 100mg; 50mg
    Market StatusPrescription
    CompanyAnchen Pharms; Amneal Pharms; Mylan Pharms; Teva; Apotex; Accord Hlthcare; Aurobindo Pharma; Cspc Ouyi Pharm; Sun Pharm Inds; Lupin; Mallinckrodt; Allied Pharma; Northstar Hlthcare; Sun Pharma Global; Par Pharm; Actavis Elizabeth; Ipca Labs; Mutual Pharm;

    6 of 6  
    Drug NameUltram er
    Drug LabelULTRAMER (tramadol hydrochloride) is a centrally acting synthetic analgesic in an extended-release formulation. The chemical name is (cis-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl) cyclohexanol hydrochloride. Its structural formula is:Figure 1The...
    Active IngredientTramadol hydrochloride
    Dosage FormTablet, extended release
    RouteOral
    Strength200mg; 300mg; 100mg
    Market StatusPrescription
    CompanyValeant Intl

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Analgesics, Opioid

    Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

    Narcotics

    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. (See all compounds classified as Narcotics.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Opioid Agonist [EPC]; Full Opioid Agonists [MoA]
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    • TABLET;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • TABLET;ORAL - 50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • TABLET;ORAL - 325MG;37.5MG
    • TABLET, EXTENDED RELEASE;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • TABLET, EXTENDED RELEASE;ORAL - 200MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • TABLET, EXTENDED RELEASE;ORAL - 300MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • TABLET, EXTENDED RELEASE;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • TABLET, EXTENDED RELEASE;ORAL - 200MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • TABLET, EXTENDED RELEASE;ORAL - 300MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
    • CAPSULE, EXTENDED RELEASE;ORAL - 100MG
    • CAPSULE, EXTENDED RELEASE;ORAL - 150MG
    • CAPSULE, EXTENDED RELEASE;ORAL - 200MG
    • CAPSULE, EXTENDED RELEASE;ORAL - 300MG
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