NORTRIPTYLINE HYDROCHLORIDE Chemical Properties

Melting point:

217-220?C

Flash point:

9℃

storage temp. 

2-8°C

solubility 

ethanol: 100 mg/mL

form 

powder

color 

white to off-white

λmax

237nm(H2O)(lit.)

Merck 

14,6715

Safety Information

Hazard Codes 

Xn,T,F

Risk Statements 

22-36/38-23/25-11-39/23/24/25-23/24/25

Safety Statements 

22-36-45-24-16-7-36/37

RIDADR 

UN 1230 3/PG 2

WGK Germany 

3

RTECS 

HP0175000

HS Code 

2921490002

Toxicity

LD50 oral in rat: 405mg/kg

MSDS

• Language:English Provider:SigmaAldrich

NORTRIPTYLINE HYDROCHLORIDE Usage And Synthesis

Chemical Properties

Off-White Solid

Originator

Aventyl,Lilly,UK,1963

Uses

Nortriptyline Hydrochloride (Amitriptyline EP Impurity C) is a tricyclic antidepressant.

Uses

Monoamine reuptake inhibitor; tricyclic antidepressant.

Definition

ChEBI: Nortriptyline hydrochloride is an organic tricyclic compound. It has a role as a geroprotector.

Manufacturing Process

A mixture of 114.5 g of 5-(3-chloropropylidene)dibenzo[a,d]cyclohepta[1,4] diene, 75 ml of benzene, and about 400 ml of methylamine is heated in an autoclave at 120°C for six hours. The excess methylamine is distilled from the reaction mixture under vacuum and the residue is stirred with 300 ml of water. Acidification of the mixture with hydrochloric acid causes the separation of the hydrochloride of 5-(3-methylaminopropylidene)dibenzo[a,d] cyclohepta[1,4]diene. The product is collected by filtration and is purified by recrystallization from a mixture of absolute ethanol and ethyl acetate. MP 210°C to 212°C.

brand name

Aventyl Hydrochloride (Lilly); Aventyl Hydrochloride (Ranbaxy); Pamelor (Tyco).

Therapeutic Function

Antidepressant

General Description

Pertinent biological and chemical properties for nortriptyline,3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)Nmethyl-1-propanamine hydrochloride, 5-(3-methyl-aminopropylidene)-10,11-hydro-5H-dibenzo[a,d] cycloheptene hydrochloride(Aventyl, Pamelor), are given previously in thediscussion of amitriptyline. Metabolic inactivation and eliminationare like those of amitriptyline. Nortriptyline is a selectiveNE transporter (NET) inhibitor.

Biological Activity

ki: 3.4 nm: blocks the norepinephrine transporter.ki: 161 nm: inhibits the serotonin transporter.nortriptyline, a dibenzocycloheptene-derivative tricyclic antidepressant, inhibits norepinephrine and serotonin transporters, which is used for short-term treatment of various forms of depression, including major depression, dysthymia, and atypical depressions. nortriptyline suppresses the norepinephrine presynaptic receptors, thus inhibiting the reuptake of this neurotransmitter and increasing the concentration in the synaptic cleft in the central nervous system.norepinephrine transporter is responsible for the sodium-chloride (na+/cl-) -dependent reuptake of extracellular norepinephrine. serotonin transporter transports serotonin from the synaptic cleft to the presynaptic neuron.

Biochem/physiol Actions

Tricyclic antidepressant that is a more potent inhibitor of the norepinephrine transporter (Ki = 3.4 nM) than the serotonin transporter (Ki = 161 nM). 5-HT2 serotonin receptor antagonist.

in vitro

nortriptyline dose-dependently dampened the spontaneous migration of human polymorphonuclear cells (pmn) at the highest concentrations (10-4 and 10-5 m). nortriptyline decreased the motility of the cells at 10-4m. chemotaxis of pmn triggered by 10-10m n-formyl-l-methionil-l-leucyl-l-phenylalanine (fmlp) was blocked by nortriptyline in a dose-dependent fashion [1].

in vivo

rats and mice were injected intraperitoneally with nortriptyline at the dose of 50, 25, 12.5 mg/kg. after 2 hours of the last injection, nortriptyline inducted little or no inhibition of the 4, α-dimethyl-meta-tyramine (h 77/77) induced depletion in a dose of 25 + 12.5 mg/kg. however, there was a partial blockade, evoked by nortriptyline in a dose of 50 + 25 mg/kg, of the h 77/77 elicited depletion in the noradrenaline nerve terminals in all the rats studied. additionally, nortriptyline also proved to be active in the brain, however, its activity was low [2].

References

[1]. sacerdote, p., bianchi, m., & panerai, a. chlorimipramine and nortriptyline but not fluoxetine and fluvoxamine inhibit human polymorphonuclear cell chemotaxis in vitro. general pharmacology: the vascular system. 1994; 25(3): 409-412.
[2]. carlsson, a., corrodi, h., fuxe, k., & hkfelt, t. effects of some antidepressant drugs on the depletion of intraneuronal brain catecholamine stores caused by 4, α-dimethyl-meta-tyramine. european journal of pharmacology.1969; 5(4): 367-373.

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