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CAS No. 71320-77-9 Density 1.206 g/cm3
Solubility soluble in water Melting Point 137 °C
Formula C13H17ClN2O2 Boiling Point 447.7 °C at 760 mmHg
Molecular Weight 268.74 Flash Point 224.6 °C
Transport Information Appearance White to off-white solid
Safety 26-39-45-36/37/39-22 Risk Codes 22-37/38-41-26/27/28
Molecular Structure Molecular Structure of 71320-77-9 (Benzamide,4-chloro-N-[2-(4-morpholinyl)ethyl]-) Hazard Symbols HarmfulXn, VeryT+

4-Chloro-N-(2-morpholin-4-ylethyl)benzamide;4-Chloro-N-(2-morpholinoethyl)benzamide;Auromid;Aurorix;Manerix;Moclaime;Moclobemide;Ro 11-1163;Ro 11-1163/000;p-Chloro-N-(2-morpholinoethyl)-benzamide;


Moclobemide History

Although clinical trials with the medicine began in 1977, it is not approved for use in the United States. It is produced by affiliates of the Hoffmann-La Roche pharmaceutical company.

Moclobemide Specification

The Moclobemide is an organic compound with the formula C13H17ClN2O2. The IUPAC name of this chemical is 4-chloro-N-(2-morpholin-4-ylethyl)benzamide. With the CAS registry number 71320-77-9, it is also named as Benzamide, 4-Chloro-N-(2-(4-morpholinyl)ethyl)-. The product's categories are Active Pharmaceutical Ingredients; All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; API's; Monoamine Oxidase. Besides, it is a white to off-white solid.

Physical properties about Moclobemide are: (1)ACD/LogP: 0.84; (2)ACD/LogD (pH 5.5): -0.6; (3)ACD/LogD (pH 7.4): 0.71; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1.91; (6)ACD/KOC (pH 5.5): 2.47; (7)ACD/KOC (pH 7.4): 50.95; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 32.78 Å2; (12)Index of Refraction: 1.55; (13)Molar Refractivity: 71.03 cm3; (14)Molar Volume: 222.8 cm3; (15)Polarizability: 28.16×10-24cm3; (16)Surface Tension: 43.3 dyne/cm; (17)Density: 1.206 g/cm3; (18)Flash Point: 224.6 °C; (19)Enthalpy of Vaporization: 70.61 kJ/mol; (20)Boiling Point: 447.7 °C at 760 mmHg; (21)Vapour Pressure: 3.29E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by 4-chloro-benzoyl chloride. This reaction will need reagent pyridine. The yield is about 71%.

Uses of Moclobemide: in efficacy studies for the treatment of major depressive disorder, moclobemide has been found to be significantly more effective than placebo, as effective as the tricyclic antidepressants (TCAs) and selective serotonin reuptake inhibitors (SSRIs), and somewhat less effective than the older, irreversible MAOIs phenelzine and tranylcypromine. In terms of tolerability, however, moclobemide was found to be comparable to the SSRIs and better tolerated than the TCAs and older MAOIs. In addition, moclobemide is occasionally used recreationaly when mixed with the prototypical psychedelic dimethyltryptamine (DMT). Orally ingested DMT is inactive, as it is rapidly metabolized by gut monoamine oxidase enzymes, hence these enzymes must be temporarily inhibited in order for DMT to pass into the bloodstream intact. The combination of DMT-containing plants and the plant-based MAO-inhibiting harmala alkaloids (harmine, harmaline) is referred to as Ayahuasca, a psychedelic brew used by several native tribes of South America in traditional spiritual ceremonies. Moclobemide serves a similar purpose to the harmala alkaloids and has been used in modern synthetic recapitulations of the Ayahuasca ritual and such a mixture, in which a synthetic MAOI is used in conjunction with DMT is commonly being referred to as "Pharmahuasca".

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and very toxic by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to respiratory system and skin and risk of serious damage to eyes. When you are using it, wear suitable gloves and eye/face protection and do not breathe dust. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccc(cc1)C(=O)NCCN2CCOCC2
(2)InChI: InChI=1/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)
(4)Std. InChI: InChI=1S/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 45mg/kg/2W-I (45mg/kg) BEHAVIORAL: CHANGE IN REM SLEEP (HUMAN)

Human Psychopharmacology. Vol. 13, Pg. 377, 1998.
mouse LD oral > 1gm/kg (1000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacology and Experimental Therapeutics. Vol. 284, Pg. 983, 1998.
mouse LD50 intraperitoneal 591mg/kg (591mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 31, Pg. 909, 1996.
rat LD50 oral 707mg/kg (707mg/kg)   United States Patent Document. Vol. #4210754,
women TDLo oral 5mg/kg/5W-I (5mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Human Psychopharmacology. Vol. 12, Pg. 81, 1997.
women TDLo oral 19mg/kg (19mg/kg) BEHAVIORAL: SLEEP


Journal of Clinical Psychiatry. Vol. 47, Pg. 438, 1986.
women TDLo oral 66mg/kg/11D-I (66mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Lancet. Vol. 346, Pg. 1032, 1995.
women TDLo oral 12600mg/kg/14 (12600mg/kg) BLOOD: THROMBOCYTOPENIA


Lancet. Vol. 347, Pg. 1329, 1996.

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