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Chemistry

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Also known as: Pyrilamine, 91-84-9, Pyranisamine, Anthisan, Dorantamin, Mepiramine

Molecular Formula

C₁₇H₂₃N₃O

Molecular Weight

285.4 g/mol

InChI Key

YECBIJXISLIIDS-UHFFFAOYSA-N

FDA UNII

HPE317O9TL

A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.

1 2D Structure

Pyrilamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine

2.1.2 InChI

InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3

2.1.3 InChI Key

YECBIJXISLIIDS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2

2.2 Other Identifiers

2.2.1 UNII

HPE317O9TL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anthisan

2. Boots Bite And Sting Relief

3. Kriptin

4. Maleate, Mepyramine

5. Maleate, Pyrilamine

6. Mepyramine Maleate

7. Pyranisamine

8. Pyrilamine

9. Pyrilamine Maleate

2.3.2 Depositor-Supplied Synonyms

1. Pyrilamine

2. 91-84-9

3. Pyranisamine

4. Anthisan

5. Dorantamin

6. Mepiramine

7. Kriptin

8. Antalergan

9. Antallergan

10. Histapyran

11. Neoantergan

12. Anhistabs

13. Anhistol

14. Antamine

15. Copsamine

16. Coradon

17. Harvamine

18. Histacap

19. Histalon

20. Histasan

21. Maranhist

22. Mepyren

23. Nyscaps

24. Paraminyl

25. Pyramal

26. Stangen

27. Statomin

28. Thylogen

29. Dipane

30. Isamin

31. Parmal

32. Neo-bridal

33. Afko-hist

34. Mepyramin

35. Stamine

36. Pyra

37. Wait's Green Mountain Antihistamine

38. Pyrilamide

39. Rp 2786

40. Nci-c60651

41. N',n'-dimethyl-n-(p-methoxybenzyl)-n-(2-pyridyl)ethylenediamine

42. 1,2-ethanediamine, N-((4-methoxyphenyl)methyl)-n',n'-dimethyl-n-2-pyridinyl-

43. Nsc13136

44. Nsc-13136

45. Chembl511

46. Hpe317o9tl

47. N1-(4-methoxybenzyl)-n2,n2-dimethyl-n1-(pyridin-2-yl)ethane-1,2-diamine

48. Chebi:6762

49. 2-((p-methoxybenzyl)(2-(dimethylamino)ethyl)amino)pyridine

50. Pyridine, 2-((p-methoxybenzyl)(2-(dimethylamino)ethyl)amino)-

51. N-(p-methoxybenzyl)-n',n'-dimethyl-n-2-pyridyl-1,2-ethanediamine

52. Mepyramine (inn)

53. [3h]mepyramine

54. [3h]pyrilamine

55. 102206-59-7

56. Ncgc00015822-09

57. 2-((2-(dimethylamino)ethyl)-(p-methoxybenzyl)amino)pyridine

58. Pyridine, 2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-

59. Mepyramine [inn]

60. Dsstox_cid_3542

61. N-[2-(dimethylamino)ethyl]-n-[(4-methoxyphenyl)methyl]pyridin-2-amine

62. 1,2-ethanediamine, N-[(4-methoxyphenyl)methyl]-n',n'-dimethyl-n-2-pyridinyl-

63. N-((4-methoxyphenyl)methyl)-n',n'-dimethyl-n-2-pyridinyl-1,2-ethanediamine

64. Dsstox_rid_77071

65. Dsstox_gsid_23542

66. Mepyramin [german]

67. P-methoxy-benzyl-.alpha.-pyridyl-dimethyl-aethylendiamin

68. 2-[[2-(dimethylamino)ethyl](p-methoxybenzyl)amino]pyridine

69. Mepiramina

70. Mepyraminum

71. Mepyramine [inn:ban]

72. Pyridine, 2-[[2-(dimethylamino)ethyl](p-methoxybenzyl)amino]-

73. N-(4-methoxybenzyl)-n',n'-dimethyl-n-pyridin-2-ylethane-1,2-diamine

74. N-(p-methoxybenzyl)-n',n'-dimethyl-n-(.alpha.-pyridyl)ethylenediamine

75. N-(p-methoxybenzyl)-n',n'-dimethyl-n-(alpha-pyridyl)ethylenediamine

76. Mepyraminum [inn-latin]

77. Mepiramina [inn-spanish]

78. N-[(4-methoxyphenyl)methyl]-n',n'-dimethyl-n-2-pyridinyl-1,2-ethanediamine

79. Cas-91-84-9

80. [11c]pyrilamine

81. [11c]-pyrilamine

82. [11c]-mepyramine

83. Ccris 4865

84. Hsdb 5187

85. Cas-59-33-6

86. Einecs 202-102-2

87. Nsc 13136

88. Unii-hpe317o9tl

89. Brn 0269019

90. 2-[(p-methoxybenzyl)[2-(dimethylamino)ethyl]amino]pyridine

91. Pyriliamine

92. Neobridal

93. 2-[[2-(dimethylamino)ethyl]-(p-methoxybenzyl)amino]pyridine

94. Pyridine, 2-[(p-methoxybenzyl)[2-(dimethylamino)ethyl]amino]-

95. Pyrlex

96. 2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)pyridine

97. 3h]pyrilamine

98. N,n-dimethyl-n'-{[4-(methyloxy)phenyl]methyl}-n'-pyridin-2-ylethane-1,2-diamine

99. N-[(4-methoxyphenyl)methyl]-n',n'-dimethyl-n-pyridin-2-ylethane-1,2-diamine

100. Histan (salt/mix)

101. Pymafed (salt/mix)

102. Antihist (salt/mix)

103. Minihist (salt/mix)

104. Spectrum_000904

105. Tocris-0660

106. Prefrin A (salt/mix)

107. Pyrilamine [mi]

108. N-(p-methoxybenzyl)-n',n'-dimethyl-n-2-pyridylethylenediamine

109. N-p-methoxybenzyl-n',n'-dimethyl-n-alpha-pyridylethylenediamine

110. P-methoxybenzyl-alpha-pyridyl-dimethyl-aethylendiamin [german]

111. N-(para-methoxybenzyl)-n',n'-dimethyl-n-2-pyridylethylenediamine

112. N-para-methoxybenzyl-n',n'-dimethyl-n-alpha-pyridylethylenediamine

113. Prestwick0_000289

114. Prestwick1_000289

115. Prestwick2_000289

116. Prestwick3_000289

117. Spectrum2_001306

118. Spectrum3_000605

119. Spectrum4_000493

120. Spectrum5_001264

121. Lopac-p-5514

122. Mepyramine [hsdb]

123. Pyrilamine [vandf]

124. Mepyramine [mart.]

125. Mepyramine [who-dd]

126. Lopac0_000890

127. Oprea1_317349

128. Schembl19114

129. Bspbio_000198

130. Bspbio_002110

131. Kbiogr_001005

132. Kbioss_001384

133. 5-22-08-00381 (beilstein Handbook Reference)

134. Bidd:gt0215

135. Divk1c_000175

136. P-methoxybenzyl-alpha-pyridyl-dimethyl-aethylendiamin

137. Spbio_001371

138. Spbio_002417

139. Bpbio1_000218

140. Ccris 1330 (salt/mix)

141. Gtpl1227

142. Gtpl3957

143. 2-[(2-dimethylaminoethyl)(p-methoxybenzyl)amino]pyridine

144. Dtxsid9023542

145. Bdbm22567

146. Kbio1_000175

147. Kbio2_001384

148. Kbio2_003952

149. Kbio2_006520

150. Kbio3_001610

151. Ninds_000175

152. Hms2089m19

153. Tox21_110230

154. Tox21_200978

155. Zinc19144216

156. N'-[(4-methoxyphenyl)methyl]-n,n-dimethyl-n'-pyridin-2-ylethane-1,2-diamine

157. Tox21_110230_1

158. Ccg-204972

159. Db06691

160. R.d. 2786

161. Sdccgsbi-0050865.p005

162. Idi1_000175

163. Wln: T6nj Bn2n1&1&1r Do1

164. Wln: T6nj Dn1r Do1&2n1&1

165. N-(p-methoxybenzyl)-n',2-ethanediamine

166. Ncgc00015822-01

167. Ncgc00015822-02

168. Ncgc00015822-03

169. Ncgc00015822-04

170. Ncgc00015822-05

171. Ncgc00015822-06

172. Ncgc00015822-07

173. Ncgc00015822-08

174. Ncgc00015822-10

175. Ncgc00015822-11

176. Ncgc00015822-12

177. Ncgc00015822-13

178. Ncgc00015822-15

179. Ncgc00015822-17

180. Ncgc00015822-21

181. Ncgc00023513-02

182. Ncgc00023513-04

183. Ncgc00023513-05

184. Ncgc00023513-06

185. Ncgc00258531-01

186. Sbi-0050865.p004

187. Ab00053539

188. Ft-0628211

189. D08183

190. Ab00053539-19

191. Ab00053539_20

192. Ab00053539_21

193. L000391

194. Q3800087

195. Brd-k97564742-050-04-6

196. Brd-k97564742-050-05-3

197. Brd-k97564742-103-01-9

198. 1, N-[(4-methoxyphenyl)methyl]-n',n'-dimethyl-n-2-pyridinyl-

199. Ethylenediamine, N',n'-dimethyl-n-(p-methoxybenzyl)-n-(2-pyridyl)-

200. Ethylenediamine,n'-dimethyl-n-(p-methoxybenzyl)-n-(2-pyridyl)-

201. N,n-dimethyl-n'-(4-methoxybenzyl)-n'-(2-pyridyl)ethylenediamine

202. N,n-dimethyl-n'-(p-methoxybenzyl)-n'-(2 -pyridyl)ethylenediamine

203. N-(p-methoxybenzyl)-n',n'-dimethyl-n-2-(pyridylethylene)diamine

204. N-p-methoxybenzyl-n',n'-dimethyl-n-.alpha.-pyridylethylenediamine

205. Pyridine, 2-[[2-(dimethylamino)ethyl][p-methoxybenzyl)amino]]-

206. N,n-dimethyl-n'-(4-methoxybenzyl)-n'-(.alpha.-pyridyl)-ethylenediaminene

207. N-(4-methoxybenzyl)-n ,n -dimethyl-n-pyridin-2-ylethane-1,2-diamine

208. N-dimethylamino-aethyl-n-p-methoxy-benzyl-.alpha.-amino-pyridin-maleat

209. 1,2-ethanediamine, N-[(4-methoxyphenyl)methyl]-n',n'-dimethyl-n-2-pyridyl-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₃N₃O
Molecular Weight	285.4 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	7
Exact Mass	285.184112366 g/mol
Monoisotopic Mass	285.184112366 g/mol
Topological Polar Surface Area	28.6 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	277
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	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Anti-Allergic Agents; Histamine H1 Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Antihistamines are indicated in the prophylactic and symptomatic treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, and allergic conjunctivitis due to inhalant allergens and foods. /Antihistamines; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 303

Antihistamines are indicated for the symptomatic treatment of pruritus associated with allergic reactions and of mild, uncomplicated allergic skin manifestations of urticaria and angioedema, in dermatographism, and in urticaria associated with transfusions. /Antihistamines; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 303

Antihistamines are also used in the treatment of pruritus associated with pityriasis rosea. /Antihistamines; NOT included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 303

For more Therapeutic Uses (Complete) data for PYRILAMINE (11 total), please visit the HSDB record page.

4.2 Drug Warning

Use is not recommended in newborn or premature infants because this age group has an increased susceptibility to anticholinergic side effects, such as central nervous system excitation, and an increased tendency toward convulsions. A paradoxical reaction characterized by hyperexcitability may occur in children taking antihistamines. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 306

Dizziness, sedation, confusion, and hypotension may be more likely to occur in geriatric patients taking antihistamines. Geriatric patients are especially susceptible to the anticholinergic side effects, such as dryness of mouth and urinary retention (especially in males), of the antihistamines. If these side effects occur and continue or are severe, medication should probably be discontinued. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 306

Prolonged use of antihistamines ... may decrease or inhibit salivary flow, thus contributing to the development of caries, periodontal disease, oral candidiasis, and discomfort. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 306

H1 antagonists are most useful in acute exudative types of allergy that present with symptoms of rhinitis, urticaria, and conjunctivitis. Their effect, however, is purely palliative and confined to the suppression of symptoms attributable to the histamine-antibody reaction. The drugs do not diminish the intensity of this reaction, which is the cause of the various hypersensitivity diseases. /Histamine Antagonist: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 587

For more Drug Warnings (Complete) data for PYRILAMINE (11 total), please visit the HSDB record page.

4.3 Minimum/Potential Fatal Human Dose

5. 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS AND 1 TEASPOONFUL FOR A 70 KG (150 LB) PERSON. /MALEATE/

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-380

4.4 Drug Indication

Indicated for the treatment of allergic conditions, symptomatic relief of hypersensitivity reaction, and treatment of pruritic skin disorders.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Sleep Aids, Pharmaceutical

Drugs used to induce SLEEP, prevent SLEEPLESSNESS, or treat SLEEP INITIATION AND MAINTENANCE DISORDERS. (See all compounds classified as Sleep Aids, Pharmaceutical.)

Anti-Allergic Agents

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

5.2 ATC Code

D - Dermatologicals

D04 - Antipruritics, incl. antihistamines, anesthetics, etc.

D04A - Antipruritics, incl. antihistamines, anesthetics, etc.

D04AA - Antihistamines for topical use

D04AA02 - Mepyramine

R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AC - Substituted ethylene diamines

R06AC01 - Mepyramine

5.3 Absorption, Distribution and Excretion

The H1 antagonists are well absorbed from the gi tract. Following oral administration, peak plasma concn are achieved in 2 to 3 hr and effects usually last 4 to 6 hr; however, some of the drugs are much longer acting ... . /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 584

... H1 antagonists are eliminated more rapidly by children than by adults and more slowly in those with severe liver disease. /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 584

5.4 Metabolism/Metabolites

MAIN SITE OF METABOLIC TRANSFORMATION IS LIVER. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 607

H1 blockers are among the many drugs that induce hepatic microsomal enzymes, and they may facilitate their own metabolism. /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 584

5.5 Mechanism of Action

Mepyramine is a histamine H1 receptor inverse agonist. It binds to a G protein-coupled form of the receptor and promotes a G protein-coupled inactive state of the H1 receptor that interferes with the Gq/11-mediated signaling. Mepyramine competes with histamine for binding at H₁-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The sedative properties of Mepyramine occur at the subcortical level of the CNS.

Antihistamines used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. They thereby prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus. Also, the anticholinergic actions of most antihistamines provide a drying effect on the nasal mucosa. /Antihistamines/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 304

H1 antagonists inhibit most responses of smooth muscle to histamine. Antagonism of the constrictor action of histamine on respiratory smooth muscle is easily shown in vivo and in vitro. /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 582

H1 antagonists strongly block the action of histamine that results in increased permeability and formation of edema and wheal. /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 583

Some H1 antagonists possess local anesthetic activity ... . /Histamine Antagonists: H1 Antagonists/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 584

For more Mechanism of Action (Complete) data for PYRILAMINE (6 total), please visit the HSDB record page.

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