Neriine

Base Information

• Chemical Name: Neriine
• CAS No.: 546-06-5
• Molecular Formula: C₂₄H₄₀N₂
• Molecular Weight: 356.595
• Hs Code.: 2939799090
• NSC Number: 347544,119994
• DSSTox Substance ID: DTXSID60859475
• Wikidata: Q105014977
• Mol file: 546-06-5.mol

Synonyms:N,N-Dimethylcon-5-enin-3-amine;Conessin;Konessin;Neriine;Wrightine;3.beta.-(Dimethylamino)con-5-ene;NSC347544;N,N-pentamethyl[?]amine;N,N,6,7,13-pentamethyl-7-azapentacyclo[10.8.0.02,9.05,9.013,18]icos-18-en-16-amine;Con-5-enine, 3.beta.-(dimethylamino)-;Conkurchine, N,18-dihydrotrimethyl-;NSC 119994;Oprea1_048812;SCHEMBL12807252;DTXSID60859475;GPLGAQQQNWMVMM-UHFFFAOYSA-N;NSC119994;3-.beta.-(Dimethylamino)con-5-enine;NSC-347544;FT-0774585;N,N-Dimethylcon-5-enin-3-amine, (3.beta.)-;Con-5-enin-3-amine,N-dimethyl-, (3.beta.)-;Con-5-enin-3-amine, N,N-dimethyl-, (3.beta.)-

Chemical Property of Neriine

Chemical Property:

• Vapor Pressure: 2.64E-08mmHg at 25°C
• Melting Point: 126-127°C
• Refractive Index: 1.5640 (estimate)
• Boiling Point: 450.4°Cat760mmHg
• PKA: 10.20±0.70(Predicted)
• Flash Point: 199.6°C
• PSA: 6.48000
• Density: 1.05g/cm³
• LogP: 4.74750
• Storage Temp.: Store at RT
• Solubility.: ethanol: ≥2mg/mL
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 356.319149284
• Heavy Atom Count: 26
• Complexity: 609

Purity/Quality:

98% ^*data from raw suppliers

Conessine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)N(C)C)C)CN1C
• Description: Conessine is a naturally occurring steroid alkaloid found in a number of plant species from the Apocynaceae family, which have been used in traditional herbal medicine as a treatment for amoebic dysentery. In a radioligand-based high-throughput screen, conessine demonstrated high affinity for both rat and human histamine H3 receptors (Kis = 5.2 and 24.5 nM, respectively) and high selectivity against histamine receptors H1, H2, and H4. Though conessine potently blocks H3 agonist-stimulated GTPγS binding in cell- and tissue-based functional assays and efficiently crosses the blood-brain barrier, it has a poor rate of CNS clearance.
• Uses: Conessine is a steroidal dibasic alkaloid with a rigid steroid-based skeleton. Conessine is a potent and selective histamine H3 receptor antagonist. antiamebic, antibacterial, antineoplastic, anesthetic (local)

Technology Process of Neriine

There total 9 articles about Neriine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

regholarrhenine C → conessine (510-73-6,546-06-5,7013-59-4,14152-37-5,14546-12-4,47469-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 24 h / Ambient temperature

2: 1.) NaBH₄, 2.) AcOH / 1.) dioxane, 6 h, 2.) dioxane, reflux, 1 h

With sodium tetrahydroborate; acetic acid; In pyridine;

DOI:10.1016/0031-9422(88)84121-9

Reference yield:

N-((3S,3aS,5aS,5bR,11aR,11bS,13aR)-2-Acetyl-3,11a-dimethyl-2,3,3a,4,5,5a,5b,6,10,11,11a,11b,12,13-tetradecahydro-1H-2-aza-pentaleno[1,6a-a]phenanthren-9-yl)-N-methyl-acetamide → conessine (510-73-6,546-06-5,7013-59-4,14152-37-5,14546-12-4,47469-35-2)

Guidance literature:

With sodium tetrahydroborate; acetic acid; Yield given. Multistep reaction; 1.) dioxane, 6 h, 2.) dioxane, reflux, 1 h;

DOI:10.1016/0031-9422(88)84121-9

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) → conessine (510-73-6,546-06-5,7013-59-4,14152-37-5,14546-12-4,47469-35-2)

Guidance literature:

With formic acid; water;

upstream raw materials:

3β-dimethylamino-con-5-en-12-one

formaldehyd

Downstream raw materials:

methyl-((3S,3aS,5aS,5bR,9S,11aR,13aR)-2,3,11a-trimethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-2-aza-pentalenol[1,6a-a]phenanthren-9-yl)-amine

Refernces

• 1、 Janot,Milliet,Lusinchi,Goutarel. "Steroidal alkaloids. LXV. Preparation of 18-nor-13 beta-cyano androstane derivatives from connessine-18-nor-13 beta-cyano testosterone". . p. 4310 - 4314. Retrieved 2007/10/04.