N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine

• ChemBase ID: 539
• Molecular Formular: C11H21N
• Molecular Mass: 167.29114
• Monoisotopic Mass: 167.16739968
• SMILES: N(C1(C(C2CC1CC2)(C)C)C)C
• Canonical SMILES: CNC1(C)C2CCC(C1(C)C)C2
• InChI: InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3
• InChIKey: IMYZQPCYWPFTAG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
• IUPAC Traditional name: mecamylaminum
• Brand Name: Inversine; Inversine hydrochloride; Mecamine; Mecamine hydrochloride; Mekamin hydrochloride; Mekamine; Mevasin hydrochloride; Mevasine; Revertina; Versamine
• Synonyms: 2-Methylamino-2,3,3-trimethylnorbornane; 2-Methylaminoisocamphane; 3-Methylaminoisocamphane; 3-Methylaminoisocamphane hydrochloride; Mecamylamine Hydrochloride; Mecamilamina; Mecamylamine

Database IDs

• CAS Number: 60-40-2
• PubChem SID: 46508607; 160964002
• PubChem CID: 4032

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.865205
• LogD (pH = 7.4): -0.6689106
• Log P: 2.3736398
• Molar Refractivity: 51.8325 cm^3
• Polarizability: 21.091114 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.13
• LOG S: -3.13
• Solubility (Water): 1.24e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.7

DETAILS

DrugBank - DB00657

• Drug Groups: approved
• Description: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool. [PubChem]
• Indication: For the treatment of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension
• Pharmacology: Mecamylamine is a potent, oral antihypertensive agent and ganglion blocker, and is a secondary amine. Mecamylamine is indicated for the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Mecamylamine reduces blood pressure in both normotensive and hypertensive individuals. A small oral dosage often produces a smooth and predictable reduction of blood pressure. Although this antihypertensive effect is predominantly orthostatic, the supine blood pressure is also significantly reduced. Mecamylamine crosses the blood-brain and placental barriers.
• Affected Organisms: Humans and other mammals
• Absorption: Mecamylamine is almost completely absorbed from the gastrointestinal tract
• Protein Binding: 40%
• Elimination: Mecamylamine is excreted slowly in the urine in the unchanged form. The rate of its renal elimination is influenced markedly by urinary pH.; Alkalinization of the urine reduces, and acidification promotes, renal excretion of mecamylamine. Mecamylamine crosses the blood-brain and placental barriers.
• External Links: Wikipedia; RxList; Drugs.com