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NCGC00024409-09

NCGC00024409-09

Synopsis, Chemistry

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Also known as: 69-09-0, Chlorpromazine hcl, Sonazine, Chloractil, Klorproman, Klorpromex

Molecular Formula

C₁₇H₂₀Cl₂N₂S

Molecular Weight

355.3 g/mol

InChI Key

FBSMERQALIEGJT-UHFFFAOYSA-N

FDA UNII

9WP59609J6

The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.

1 2D Structure

NCGC00024409-09

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine;hydrochloride

2.1.2 InChI

InChI=1S/C17H19ClN2S.ClH/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20;/h3-4,6-9,12H,5,10-11H2,1-2H3;1H

2.1.3 InChI Key

FBSMERQALIEGJT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

9WP59609J6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aminazine

2. Chlorazine

3. Chlordelazine

4. Chlorpromazine

5. Contomin

6. Fenactil

7. Hydrochloride, Chlorpromazine

8. Largactil

9. Propaphenin

10. Thorazine

2.3.2 Depositor-Supplied Synonyms

1. 69-09-0

2. Chlorpromazine Hcl

3. Sonazine

4. Chloractil

5. Klorproman

6. Klorpromex

7. Marazine

8. Norcozine

9. Promacid

10. Hebanil

11. Promapar

12. Hybernal

13. Lomazine

14. Neurazine

15. Plegomazin

16. Promachel

17. Promexin

18. Taroctyl

19. Tranzine

20. Hibernal

21. Unitensen

22. Nci-c05210

23. Chlorpromazine (hydrochloride)

24. Aminazin Monohydrochloride

25. Fenactil Monohydrochloride

26. Chloropromazine Monohydrochloride

27. Ampliactil Monohydrochloride

28. Hibanil

29. Chlorpromazinium Chloride

30. Chlorpromazine Monohydrochloride

31. [3-(2-chloro-10h-phenothiazin-10-yl)propyl]-dimethylamine Hydrochloride

32. Chloropromazine Hydrochloride

33. Propaphen

34. 10-(3-dimethylaminopropyl)-2-chlorophenothiazine Monohydrochloride

35. Thorazine Hydrochloride

36. 3-(2-chlorophenothiazin-10-yl)-n,n-dimethylpropan-1-amine;hydrochloride

37. 3-(2-chloro-10h-phenothiazin-10-yl)-n,n-dimethylpropan-1-amine Hydrochloride

38. Mls000069401

39. Chebi:3649

40. 2-chloro-10-(3-(dimethylamino)propyl)phenothiazine Monohydrochloride

41. 10h-phenothiazine-10-propanamine, 2-chloro-n,n-dimethyl-, Monohydrochloride

42. Nsc-17479

43. 9wp59609j6

44. 69-09-0 (hcl)

45. Aminazinum

46. Megatil

47. Smr000058254

48. 2-chloro-10-(3-dimethylaminopropyl)phenothiazine Hydrochloride

49. 4560 Rp Hydrochloride

50. Chlorpromazine, Hydrochloride

51. Contomin Hydrochloride

52. Megaphen Hydrochloride

53. Phenothiazine Hydrochloride

54. Largactil Monohydrochloride

55. Cpz (van)

56. Nsc17479

57. Ccris 6221

58. [3-(2-chloro-10h-phenothiazin-10-yl)propyl]dimethylamine Hydrochloride

59. Cas-69-09-0

60. Sr-01000000012

61. Einecs 200-701-3

62. Nsc 17479

63. Chloropromazin Hydrochloride

64. Largaktyl

65. Ai3-28023

66. Unii-9wp59609j6

67. Prestwick_58

68. Sonazine (tn)

69. Chlorpromazine Hydrochloride Intensol

70. Mfcd00012654

71. Chlorpromazine Chloride

72. Ac1lcwf1

73. Chlorpromazine Hydrochloride [usp:ban:jan]

74. Opera_id_1294

75. Dsstox_cid_4827

76. Chlorpromazini Hydrochloridum

77. Chembl1713

78. Dsstox_rid_77545

79. Dsstox_gsid_24827

80. Schembl41771

81. Mls001148603

82. Mls002222157

83. Chlorpromazin-d6 Hydrochloride

84. Dtxsid7024827

85. Hy-b0407a

86. Chlorpromazine Hydrochloride, 98%

87. Hms1568m09

88. Bcp30284

89. Tox21_300517

90. Tox21_500249

91. Nsc226514

92. S2456

93. Akos005111082

94. Phenothiazine, 2-chloro-10-(3-(dimethylamino)propyl)-, Monohydrochloride

95. Ccg-220064

96. Ccg-221553

97. Chlorpromazine-[13c,d3] Hydrochloride

98. Lp00249

99. Nc00552

100. 7-[diethylamino]coumarin-3-carbonylazide

101. Chlorpromazine Hydrochloride (jp17/usp)

102. Chlorpromazine Hydrochloride [mi]

103. Ncgc00024409-09

104. Ncgc00093711-01

105. Ncgc00093711-02

106. Ncgc00180973-01

107. Ncgc00254272-01

108. Ncgc00260934-01

109. Ac-10573

110. Chlorpromazine Hydrochloride [jan]

111. Ls-14587

112. Chlorpromazine Hydrochloride [mart.]

113. Chlorpromazine Hydrochloride [vandf]

114. C-165

115. Chlorpromazine Hydrochloride [usp-rs]

116. Chlorpromazine Hydrochloride [who-dd]

117. Chlorpromazine Hydrochloride [who-ip]

118. Chlorpromazine Hydrochloride, >=98% (tlc)

119. Eu-0100249

120. Ft-0623715

121. Ft-0665009

122. Sw196373-5

123. C 8138

124. C07952

125. Chlorpromazine, Hydrochloride - Cas 69-09-0

126. D00789

127. D89519

128. Mls-0090820.0001

129. Chlorpromazine Hydrochloride [green Book]

130. Wln: T C666 Bn Isj B3n1&1 Eg &gh

131. 012c654

132. Chlorpromazine Hydrochloride [ep Impurity]

133. Chlorpromazine Hydrochloride [ep Monograph]

134. Chlorpromazine Hydrochloride [orange Book]

135. Chlorpromazine Hydrochloride [usp Monograph]

136. Chlorpromazini Hydrochloridum [who-ip Latin]

137. Q-200842

138. Sr-01000000012-2

139. Sr-01000000012-9

140. Chlorpromazine Hydrochloride 100 Microg/ml In Methanol

141. Q27106159

142. Z1259155914

143. 2-chloro-10-(3-dimethylaminopropyl) Phenothiazine Hydrochloride

144. Chlorpromazine Hydrochloride, Meets Usp Testing Specifications

145. Chlorpromazine Hydrochloride, Vetranal(tm), Analytical Standard

146. 2-chloro-10-(3-dimethylaminopropyl)phenothiazine Monohydrochloride

147. 2-chloro-10-[3-(dimethylamino)-1-propyl]phenothiazine Hydrochloride

148. Chlorpromazine Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

149. 10h-phenothiazine-10-propanamine Hydrochloride, 2-chloro-n,n-dimethyl-

150. 3-(2-chlorophenothiazin-10-yl)-n,n-dimethylpropan-1-amine;hydrochloride.

151. Chlorpromazine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

152. 10h-phenothiazine-10-propanamine, 2-chloro-n,n-dimethyl-, Hydrochloride (1:1)

153. Chlorpromazine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

154. Chlorpromazine Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.3.3 Other Synonyms

1. 2-chlorophenothiazine

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₀Cl₂N₂S
Molecular Weight	355.3 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	354.0724252 g/mol
Monoisotopic Mass	354.0724252 g/mol
Topological Polar Surface Area	31.8 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	339
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Chlorpromazine hydrochloride
Drug Label	DESCRIPTION Chlorpromazine hydrochloride, a dimethylamine derivative of phenothiazine, has a chemical formula of 2-chloro-10-[3(-dimethylamino) propyl] phenothiazine monohydochloride. It is available in tablets for oral administration. It has the fol...
Active Ingredient	Chlorpromazine hydrochloride
Dosage Form	Injectable; Tablet
Route	Injection; Oral
Strength	25mg/ml; 200mg; 100mg; 25mg; 50mg; 10mg
Market Status	Prescription
Company	Hikma Maple; Usl Pharma; Sandoz

2 of 2
Drug Name	Chlorpromazine hydrochloride
Drug Label	DESCRIPTION Chlorpromazine hydrochloride, a dimethylamine derivative of phenothiazine, has a chemical formula of 2-chloro-10-[3(-dimethylamino) propyl] phenothiazine monohydochloride. It is available in tablets for oral administration. It has the fol...
Active Ingredient	Chlorpromazine hydrochloride
Dosage Form	Injectable; Tablet
Route	Injection; Oral
Strength	25mg/ml; 200mg; 100mg; 25mg; 50mg; 10mg
Market Status	Prescription
Company	Hikma Maple; Usl Pharma; Sandoz

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Phenothiazines [CS]; Phenothiazine [EPC]