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    Chemistry

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    Also known as: 63-92-3, Phenoxybenzamine hcl, Dibenzyline, N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine hydrochloride, Dibenzyline hydrochloride, Dibenzyran
    Molecular Formula
    C18H23Cl2NO
    Molecular Weight
    340.3  g/mol
    InChI Key
    VBCPVIWPDJVHAN-UHFFFAOYSA-N
    FDA UNII
    X1IEG24OHL
    Phenoxybenzamine HCl
    An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator.
    1 2D Structure

    Phenoxybenzamine HCl

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-benzyl-N-(2-chloroethyl)-1-phenoxypropan-2-amine;hydrochloride
    2.1.2 InChI
    InChI=1S/C18H22ClNO.ClH/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17;/h2-11,16H,12-15H2,1H3;1H
    2.1.3 InChI Key
    VBCPVIWPDJVHAN-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(COC1=CC=CC=C1)N(CCCl)CC2=CC=CC=C2.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    X1IEG24OHL
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Dibenylene

    2. Dibenyline

    3. Dibenziran

    4. Dibenzylin

    5. Dibenzyline

    6. Dibenzyran

    7. Hydrochloride, Phenoxybenzamine

    8. Phenoxybenzamine

    2.3.2 Depositor-Supplied Synonyms

    1. 63-92-3

    2. Phenoxybenzamine Hcl

    3. Dibenzyline

    4. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine Hydrochloride

    5. Dibenzyline Hydrochloride

    6. Dibenzyran

    7. Dibenzyline Chloride

    8. Phenoxybenzamine Chloride

    9. Phenoxybenzamine (hydrochloride)

    10. Bensylyt Nen

    11. Dibenzylin

    12. Phenoxybenzamine.hcl

    13. Nci-c01661

    14. Nsc-37448

    15. 2-(n-benzyl-2-chloroethylamino)-1-phenoxypropane Hydrochloride

    16. N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)benzylamine Hydrochloride

    17. Mls000069374

    18. Chebi:8078

    19. Nsc 37448

    20. 63-92-3 (hcl)

    21. Smr000058422

    22. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine;hydrochloride

    23. Dsstox_cid_1127

    24. N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)benzenemethanamine Hydrochloride

    25. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-,hydrochloride

    26. Dsstox_rid_75958

    27. Dsstox_gsid_21127

    28. N-2-phenoxyisopropyl-n-benzyl-chloroethylamine Hydrochloride

    29. Benzyl(2-chloroethyl)(1-methyl-2-phenoxyethyl)amine Hydrochloride

    30. X1ieg24ohl

    31. Benzylamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-, Hydrochloride

    32. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-, Hydrochloride

    33. Phenoxybenzamine Hydrochloride (usp)

    34. Sr-01000000017

    35. Dibenzylene

    36. Dibenzyline (tn)

    37. Mfcd00055152

    38. Pob Hcl

    39. Cpd000058422

    40. Opera_id_300

    41. Cas-63-92-3

    42. Phenoxybenzaminehydrochloride

    43. Schembl50729

    44. Bensylyte Hydrochloride

    45. Mls002222313

    46. Spectrum2300176

    47. Chembl1200787

    48. Dtxsid0021127

    49. Hy-b0431a

    50. Hms1570n10

    51. Pharmakon1600-02300176

    52. Phenoxybenzamine Hydrochloride,(s)

    53. Bcp28467

    54. Nsc37448

    55. Tox21_201588

    56. Tox21_302978

    57. Wln: G2n1r&y1&1or &gh

    58. Ccg-39614

    59. Nsc759572

    60. Akos015966790

    61. Ac-8077

    62. Lp00235

    63. Nc00598

    64. Nsc-759572

    65. Ncgc00089748-02

    66. Ncgc00089748-06

    67. Ncgc00093699-01

    68. Ncgc00093699-02

    69. Ncgc00093699-03

    70. Ncgc00093699-04

    71. Ncgc00256370-01

    72. Ncgc00259137-01

    73. As-16927

    74. Phenoxybenzamine Hydrochloride [mi]

    75. Db-054579

    76. B-019

    77. D0158

    78. Eu-0100235

    79. Ft-0603264

    80. Ft-0673569

    81. Ft-0673570

    82. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan

    83. Phenoxybenzamine Hydrochloride [iarc]

    84. Phenoxybenzamine Hydrochloride [vandf]

    85. S2499

    86. Sw197327-3

    87. En300-52514

    88. Phenoxybenzamine Hydrochloride [mart.]

    89. C07436

    90. D00507

    91. Phenoxybenzamine Hydrochloride [usp-rs]

    92. Phenoxybenzamine Hydrochloride [who-dd]

    93. Phenoxybenzamine Hydrochloride, >=97%, Powder

    94. 055p152

    95. J-009731

    96. Phenoxybenzamine Hydrochloride [orange Book]

    97. Sr-01000000017-2

    98. Sr-01000000017-6

    99. Phenoxybenzamine Hydrochloride [usp Monograph]

    100. Q27107723

    101. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine;hydron;chloride

    102. N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)benzylamine, Hydrochloride

    103. N-2-phenoxyisopropyl-n-benzyl-.beta.-chloroethylamine Hydrochloride

    104. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-, Hydrochloride (1:1)

    105. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-,hcl

    106. Phenoxybenzamine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    107. 34238-85-2

    108. Phenoxybenzamine Hcl Pound>>nci-c01661 Pound>> Nci C01661 Pound>> Ncic01661 Pound>>nsc 37448 Pound>>nsc37448 Pound>>nsc-37448

    109. Phenoxybenzamine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-11-20
    3 Chemical and Physical Properties
    Molecular Weight 340.3 g/mol
    Molecular Formula C18H23Cl2NO
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count8
    Exact Mass339.1156697 g/mol
    Monoisotopic Mass339.1156697 g/mol
    Topological Polar Surface Area12.5 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity262
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameDibenzyline
    Drug LabelEach Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
    Active IngredientPhenoxybenzamine hydrochloride
    Dosage FormCapsule
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyWellspring Pharm

    2 of 4  
    Drug NamePhenoxybenzamine hydrochloride
    PubMed HealthPhenoxybenzamine (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelEach Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
    Active IngredientPhenoxybenzamine hydrochloride
    Dosage FormCapsule
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyRoxane

    3 of 4  
    Drug NamePhenoxybenzamine hydrochloride
    PubMed HealthPhenoxybenzamine (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelEach Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
    Active IngredientPhenoxybenzamine hydrochloride
    Dosage FormCapsule
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyRoxane

    4 of 4  
    Drug NameDibenzyline
    Drug LabelEach Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
    Active IngredientPhenoxybenzamine hydrochloride
    Dosage FormCapsule
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyWellspring Pharm

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Adrenergic alpha-Antagonists

    Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)

    Antihypertensive Agents

    Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

    Vasodilator Agents

    Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    alpha-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]

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