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Chemistry

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Also known as: Yohimbin, 146-48-5, Quebrachin, Quebrachine, Corynine, Aphrodine
Molecular Formula
C21H26N2O3
Molecular Weight
354.4  g/mol
InChI Key
BLGXFZZNTVWLAY-SCYLSFHTSA-N
FDA UNII
2Y49VWD90Q

Yohimbine
A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.
1 2D Structure

Yohimbine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
2.1.2 InChI
InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
2.1.3 InChI Key
BLGXFZZNTVWLAY-SCYLSFHTSA-N
2.1.4 Canonical SMILES
COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
2.1.5 Isomeric SMILES
COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O
2.2 Other Identifiers
2.2.1 UNII
2Y49VWD90Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aphrodine Hydrochloride

2. Aphrodyne

3. Corynanthine

4. Corynanthine Tartrate

5. Hydrochloride, Aphrodine

6. Hydrochloride, Yohimbine

7. Pluriviron

8. Rauhimbine

9. Rauwolscine

10. Tartrate, Corynanthine

11. Yocon

12. Yohimbin Spiegel

13. Yohimbine Houd

14. Yohimbine Hydrochloride

15. Yohimex

2.3.2 Depositor-Supplied Synonyms

1. Yohimbin

2. 146-48-5

3. Quebrachin

4. Quebrachine

5. Corynine

6. Aphrodine

7. Yohimbic Acid Methyl Ester

8. Aphrosol

9. (+)-yohimbine

10. Johimbin

11. Actibine

12. Yohimbinum

13. 17-hydroxyyohimban-16-carboxylic Acid Methyl Ester

14. Yohimban-16-carboxylic Acid, 17-hydroxy-, Methyl Ester, (16alpha,17alpha)-

15. Chembl15245

16. 2y49vwd90q

17. 17alpha-hydroxyyohimban-16alpha-carboxylic Acid Methyl Ester

18. Chebi:10093

19. (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic Acid Methyl Ester

20. Methyl 17alpha-hydroxyyohimban-16alpha-carboxylate

21. Dsstox_cid_20130

22. Dsstox_rid_79446

23. Dsstox_gsid_40130

24. Methyl (1s,15r,18s,19r,20s)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

25. Methyl (1s,15r,18s,19r,20s)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

26. Yohimbine Chloride

27. Chembl537669

28. Yohimbine (dcf)

29. Cas-146-48-5

30. Amberlite Cg 400

31. Amberlite Cg-400

32. Methyl Hydroxy[?]carboxylate

33. Einecs 205-672-0

34. Brn 0097276

35. Trans-quinolizidine Yohimbine

36. Unii-2y49vwd90q

37. Yohimbe Bark

38. Yohimbe Hydrochloride

39. Ccris 9415

40. Sr-01000075297

41. Benz[g]indolo[2,3-a]quinolizine, Yohimban-16-carboxylic Acid Deriv.

42. Yohimbehydrochloride

43. Yohimbe Bark Extract

44. 37247-87-3

45. Nsc19509

46. Yohimbine [mi]

47. Methyl (2s,13bs,14as,1r,4ar)-2-hydroxy-1,2,3,4,5,8,14,13b,14a,4a-decahydrobenz O[1,2-g]indolo[2,3-a]quinolizinecarboxylate

48. Prestwick0_000584

49. Prestwick1_000584

50. Prestwick2_000584

51. Prestwick3_000584

52. Yohimban-16-alpha-carboxylic Acid, 17-alpha-hydroxy-, Methyl Ester

53. Yohimbe Extract Yohimbine

54. Yohimbine [vandf]

55. Yohimbinum [hpus]

56. Cid_6169

57. Cid_8969

58. Yohimbine [who-dd]

59. Lopac0_001210

60. Schembl33954

61. Bspbio_000428

62. Bspbio_001236

63. Gtpl102

64. Kbiogr_000576

65. Kbioss_000576

66. 4-25-00-01237 (beilstein Handbook Reference)

67. Mls000728591

68. Spbio_002647

69. Bpbio1_000472

70. Yohimbol-16alpha-carboxylic Acid, Methyl Ester (6ci)

71. Dtxsid9040130

72. Bcbcmap01_000032

73. Kbio2_000576

74. Kbio2_003144

75. Kbio2_005712

76. Kbio3_001031

77. Kbio3_001032

78. Bio1_000455

79. Bio1_000944

80. Bio1_001433

81. Bio2_000458

82. Bio2_000938

83. Hms1362n17

84. Hms1792n17

85. Hms1990n17

86. Hms2089g19

87. Hms2234c18

88. Zinc3860825

89. Tox21_110019

90. Bdbm50013515

91. Bdbm50203564

92. Mfcd00005093

93. Akos015902024

94. Tox21_110019_1

95. Yohimban-16-.alpha.-carboxylic Acid, 17-.alpha.-hydroxy-, Methyl Ester

96. Yohimban-16alpha-carboxylic Acid, 17alpha-hydroxy-, Methyl Ester (8ci)

97. Ccg-205284

98. Cs-5173

99. Db01392

100. Gs-5751

101. Sdccgsbi-0051177.p002

102. Idi1_002213

103. Mrf-0000020

104. Smp1_000320

105. Ncgc00013260-01

106. Ncgc00025018-05

107. Ncgc00025018-06

108. Ncgc00025018-07

109. Ncgc00025018-10

110. Ncgc00025018-11

111. Ncgc00025018-17

112. Hy-12715

113. Smr000470778

114. 17a-hydroxy-16a-methoxycarbonyl-yohimbane

115. 65y190

116. C09256

117. D08685

118. H10057

119. Q412226

120. Sr-01000075297-5

121. Brd-k35586044-001-02-6

122. Brd-k35586044-003-03-0

123. Brd-k35586044-003-11-3

124. 17.alpha.-hydroxy-20-.alpha.-yohimban-16-.beta.-carboxylic Acid, Methyl Ester

125. Yohimban-16-carboxylic Acid, 17-hydroxy-, Methyl Ester, (16alpha,17alpha)- (9ci)

126. (1r,2s,4ar,13bs,14as)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic Acid Methyl Ester Hydrochloride

127. 103834-06-6

2.4 Create Date
2005-05-18
3 Chemical and Physical Properties
Molecular Weight 354.4 g/mol
Molecular Formula C21H26N2O3
XLogP32.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass354.19434270 g/mol
Monoisotopic Mass354.19434270 g/mol
Topological Polar Surface Area65.6 Ų
Heavy Atom Count26
Formal Charge0
Complexity555
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Indicated as a sympatholytic and mydriatic. Impotence has been successfully treated with yohimbine in male patients with vascular or diabetic origins and psychogenic origins.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Yohimbine is an indolalkylamine alkaloid with chemical similarity to reserpine. Yohimbine blocks presynaptic alpha-2 adrenergic receptors. Its action on peripheral blood vessels resembles that of reserpine, though it is weaker and of short duration. Yohimbine's peripheral autonomic nervous system effect is to increase parasympathetic (cholinergic) and decrease sympathetic (adrenergic) activity. It is to be noted that in male sexual performance, erection is linked to cholinergic activity and to alpha-2 adrenergic blockade which may theoretically result in increased penile inflow, decreased penile outflow or both. Yohimbine exerts a stimulating action on the mood and may increase anxiety. Such actions have not been adequately studied or related to dosage although they appear to require high doses of the drug. Yohimbine has a mild anti-diuretic action, probably via stimulation of hypothalmic center and release of posterior pituitary hormone. Reportedly Yohimbine exerts no significant influence on cardiac stimulation and other effects mediated by (beta)-adrenergic receptors. Its effect on blood pressure, if any, would be to lower it; however, no adequate studies are at hand to quantitate this effect in terms of Yohimbine dosage.


5.2 MeSH Pharmacological Classification

Adrenergic alpha-2 Receptor Antagonists

Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Antagonists.)


Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)


Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)


5.3 ATC Code

G04BE04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BE - Drugs used in erectile dysfunction

G04BE04 - Yohimbine


5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).


5.5 Metabolism/Metabolites

Yohimbine appears to undergo extensive metabolism in an organ of high flow such as the liver or kidney, however, the precise metabolic fate of yohimbine has not been fully determined.


5.6 Biological Half-Life

Elimination half-life is approximately 36 minutes.


5.7 Mechanism of Action

Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. The exact mechanism for its use in impotence has not been fully elucidated. However, yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. Yohimbine-mediated norepinephrine release at the level of the corporeal tissues may also be involved. In addition, beneficial effects may involve other neurotransmitters such as dopamine and serotonin and cholinergic receptors.


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25-Mar-2021
26-Oct-2024
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