dimethyl({3-[(2Z)-tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene]propyl})amine hydrochloride

• ChemBase ID: 105418
• Molecular Formular: C20H24ClN
• Molecular Mass: 313.86426
• Monoisotopic Mass: 313.15972745
• SMILES: Cl.CN(C)CC/C=C\1/c2ccccc2CCc2ccccc12
• Canonical SMILES: CN(CC/C=C/1\c2ccccc2CCc2c1cccc2)C.Cl
• InChI: InChI=1S/C20H23N.ClH/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20;/h3-6,8-12H,7,13-15H2,1-2H3;1H
• InChIKey: KFYRPLNVJVHZGT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; dimethyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; dimethyl({3-[(2E)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; dimethyl(3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine hydrochloride; dimethyl(3-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amine hydrochloride
• IUPAC Traditional name: dimethyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; dimethyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; dimethyl({3-[(2E)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; amitriptyline hydrochloride; dimethyl(3-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amine hydrochloride
• Synonyms: Amitriptyline hydrochloride; 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine hydrochloride; 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine Hydrochloride; Adepril; Amineurin; Elavil; Endep; Euplit; Laroxyl; Tryptanol; Elavil Hydrochloride; Domical; Tryptizol; AMITRIPTYLINE HYDROCHLORIDE; Amitriptyline HCl; 阿米替林 盐酸盐

Database IDs

• CAS Number: 549-18-8
• EC Number: 208-964-6
• MDL Number: MFCD00012537
• PubChem SID: 24278073; 162092174
• PubChem CID: 11065

CALCULATED PROPERTIES

• H Donor: 0
• LogD (pH = 5.5): 1.3778014
• LogD (pH = 7.4): 2.477238
• Log P: 4.809535
• Molar Refractivity: 101.5072 cm^3
• Polarizability: 35.254482 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• H Acceptors: 1

PROPERTIES

Physical Property

• Solubility: Chloroform; ethanol: soluble; H2O: soluble; Methanol
• Apperance: white to off-white powder; White to Off-White Solid
• Melting Point: 197-198°C; 198 - 200°C

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• RTECS: HO9450000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 63-22; R:22
• Safety Statements: 22; S:36/37/39
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H361
• GHS Precautionary statements: P281-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: 5-HT Receptor
• Gene Information: human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

Product Information

• Purity: ≥98% (TLC); 99%
• Salt Data: HCl; HCl
• Empirical Formula (Hill Notation): C20H23N · HCl

DETAILS

MP Biomedicals - 02190154

Hydrochloride

Sigma Aldrich - A8404

Features and Benefits
Shelf-life of the powder is at least three years.
Application
Amitriptyline hydrochloride is a tricyclic antidepressant drug. Amitriptyline hydrochloride inhibits the norepinephrine and serotonin transporters but has a high affinity for α1-adrenergic, serotonin and muscarinic acetylcholine receptors.
Biochem/physiol Actions
三环抗抑郁剂；抑制分别具有 100nM 和 14.7nM Kis 的去甲肾上腺素和 5-羟色胺转运蛋白；对 α1-肾上腺素受体、5-羟色胺和毒蕈碱型乙酰胆碱受体具有高度的体外亲和力。

Sigma Aldrich - 284629

Biochem/physiol Actions
Tricyclic antidepressant; inhibits the norepinephrine and serotonin transporters with Kis of 100 nM and 14.7 nM, respectively; high in vitro affinity for α1-adrenoceptors, serotonin and muscarinic acetylcholine receptors.

Toronto Research Chemicals - A633350

Antidepressant.

REFERENCES

• Blessel, K.W., et al.: Anal. Profiles Drug Subs., 3, 127 (1974)
• Tobe, A., et al.: Arzneim.-Forsch., 31, 1278 (1974)