Conessine

Title: Conessine
CAS Registry Number: 546-06-5
CAS Name: (3b)-N,N-Dimethylcon-5-enin-3-amine
Additional Names: 3b-(dimethylamino)con-5-enine; neriine; roquessine; wrightine
Molecular Formula: C24H40N2
Molecular Weight: 356.59
Percent Composition: C 80.84%, H 11.31%, N 7.86%
Literature References: Antiamebic, antifungal principle in Kurchi bark, the bark of Holarrhena anti-dysenterica Wall., Apocynaceae, native to India; also found in African species, such as H. africana A.DC.; H. congolensis Stapf; H. wulfsbergii Stapf, and H. febrifuga Klotzsch, Apocynaceae. Isoln: Haines, Trans. Med. Soc. Bombay 4, 28 (1858); Warnecke, Ber. 19, 60 (1886); Bertho, Arch. Pharm. 277, 237 (1939); Siddiqui, Pillay, J. Indian Chem. Soc. 9, 553 (1932). Structure: Haworth et al., J. Chem. Soc. 1953, 1102; Haworth, McKenna, Chem. Ind. (London) 1957, 1510; Bertho, Götz, Ann. 619, 96 (1958). Discussion of structure in Fieser, Fieser, Steroids (New York, 1959), p 858. Synthesis from D5-pregnene-3b,20b-diol: Barton, Morgan, Proc. Chem. Soc. London 1961, 206; J. Chem. Soc. 1962, 622. Total synthesis: Marshall, Johnson, J. Am. Chem. Soc. 84, 1485 (1962); Stork et al., ibid. 2018; Nagata et al., Tetrahedron Lett. 1963, 869.
Properties: Leaflets or broad plates from acetone, mp 127-128.5°. [a]D20 +25.3° (c = 0.7 in abs alc). Sparingly sol in water.
Melting point: mp 127-128.5°
Optical Rotation: [a]D20 +25.3° (c = 0.7 in abs alc)
Derivative Type: Dihydrochloride monohydrate
Molecular Formula: C24H40N2.2HCl.H2O
Molecular Weight: 447.52
Percent Composition: C 64.41%, H 9.91%, N 6.26%, Cl 15.84%, O 3.58%
Properties: Crystals, sol in water, mp >340°. [a]D20 +9.3° (c = 0.9 in H2O).
Melting point: mp >340°
Optical Rotation: [a]D20 +9.3° (c = 0.9 in H2O)
Derivative Type: Dihydrobromide
CAS Registry Number: 5913-82-6
Molecular Formula: C24H40N2.2HBr
Molecular Weight: 518.41
Percent Composition: C 55.60%, H 8.17%, N 5.40%, Br 30.83%
Properties: Crystals, dec 340°. Very bitter taste. [a]D20 +7.0° (c = 5 in H2O). Sol in water. Slightly sol in 95% ethanol. Very slightly sol in ether. Practically insol in petr ether.
Optical Rotation: [a]D20 +7.0° (c = 5 in H2O)
Congressane Conhydrine Coniferin Coniferyl Alcohol Conium Fruit

Conessine
Conessine.png
Identifiers
CAS number 546-06-5 YesY
PubChem 441082
ChemSpider 389885 N
MeSH Conessine
ChEMBL CHEMBL191703 N
Jmol-3D images Image 1
Properties
Molecular formula C24H40N2
Molar mass 356.5878
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Conessine is a steroid alkaloid found in a number of plant species from the Apocynaceae family, including Holarrhena floribunda,[1] Holarrhena antidysenterica[2] and Funtumia elastica,[3] several of which are used in traditional herbal medicine as a treatment for amoebic dysentery.[4] It acts as a histamine antagonist, selective for the H3 subtype (with an affinity of pKi=8.27; Ki~5nM).[5] It was also found to have long CNS clearance times, high blood-brain barrier penetration and high affinity for the adrenergic receptors.[6]