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Levonordefrin

Levonordefrin structure

CAS No:
829-74-3
Formula:
C9H13NO3
Chemical Name:
Levonordefrin
Synonyms:
1,2-Benzenediol,4-[(1R,2S)-2-amino-1-hydroxypropyl]-;Benzyl alcohol,α-(1-aminoethyl)-3,4-dihydroxy-,erythro-(-)-;1,2-Benzenediol,4-(2-amino-1-hydroxypropyl)-,[R-(R*,S*)]-;l-Norephedrine,3,4-dihydroxy-;4-[(1R,2S)-2-Amino-1-hydroxypropyl]-1,2-benzenediol;l-α-(1-Aminoethyl)-3,4-dihydroxybenzyl alcohol;Levonordefrin;(-)-α-Methylnoradrenaline;(-)-Nordefrin;(-)-erythro-α-Methylnoradrenaline;BA 2818;D-(-)-Cobefrin;L-α-Methylnoradrenaline;(-)-Cobefrin;Corbadrine;l-Cobefrin;(1R,2S)-(-)-3,4-Dihydroxynorephedrine;4-((1R,2S)-2-Amino-1-hydroxypropyl)benzene-1,2-diol;Neo-cobefrin;13725-11-6;16906-83-5;18829-78-2;34535-70-1
Categories:
Organic Chemistry > Amides

Description

White Powder

Solid

Alpha-methylnoradrenaline is a catecholamine in which the 2-aminoethyl group is substituted with a hydroxy group at C-1 and a methyl group at C-2, with configurations 1R,2S. A metabolite of alpha-methyl-L-dopa, it is an alpha2-adrenergic agonist and acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry. It has a role as an alpha-adrenergic agonist, a vasoconstrictor agent and a nasal decongestant.|Levonordefrin acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry.|Levonordefrin is the levoisomer of nordefrin, a synthetic catecholamine and norepinephrine derivative with sympathomimetic and antihypertensive effects. Levonordefrin's antihypertensive effect is exerted through activation of alpha 2-adrenergic receptors in the cardiovascular control center of the CNS thereby suppressing the sympathetic output from the brain and subsequently lowering blood pressure. Levonordefrin binds to and activates peripheral alpha 2- adrenergic receptors, thereby causing vasoconstriction.|A norepinephrine derivative used as a vasoconstrictor agent.

Levonordefrin Basic Attributes

Molecular Weight：

183.2

Exact Mass：

183.20

UNII：

V008L6478D

NSC Number：

757084

DSSTox ID：

DTXSID6046349

NCI Thesaurus Code：

C47584

HScode：

2922509090

Characteristics

PSA：

86.7

XLogP3：

1.17870

Appearance：

white to light brown

Density：

1.328g/cm3

Melting Point：

212-215°C dec.

Boiling Point：

431.575ºC at 760 mmHg

Flash Point：

214.809ºC

Refractive Index：

1.633

Water Solubility：

DMSO: soluble 5mg/mL, clear (warmed)

Storage Conditions：

−20°C

Toxicity：

LD50 in mice (mg/kg): 12.6 i.v. (Luduena)

Specific rotation：

D25 -31.0° (c = 0.5 in 0.01N HCl)

Safety Information

Transport codes：

UN 2811 6.1 / PGII

wgk germany：

hazard class code：

20/21/22-36/37/38

safety instructions：

26-36

Marks：

Precautionary statement(s)：

P261-P280-P301 + P312 + P330-P305 + P351 + P338

Hazard Statements：

H302 + H312 + H332-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Used as a topical nasal decongestant and vasoconstrictor in dentistry.

Pharmacology：

Levonordefrin is a sympathomimetic amine used as a vasoconstrictor in local anesthetic solutions. It has pharmacologic activity similar to that of Epinephrine but it is more stable than Epinephrine. In equal concentrations, Levonordefrin is less potent than Epinephrine in raising blood pressure, and as a vasoconstrictor.

MeSH：

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

Mechanism of Action：

It is designed to mimic the molecular shape of adrenaline. It binds to alpha-adrenergic receptors in the nasal mucosa. Here it can, therefore, cause vasoconstriction.

MeSH Entry Terms：

3,4 Dihydroxynorephedrine

Levonordefrin Use and Manufacturing

Uses

Vasoconstrictor;Adrenergic receptor agonist

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:183.20
XLogP3:-0.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:183.08954328
Monoisotopic Mass:183.08954328
Topological Polar Surface Area:86.7
Heavy Atom Count:13
Complexity:165
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes