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D030

Sigma-Aldrich

R(−)-2,10,11-Trihydroxy-N-propyl-noraporphine hydrobromide hydrate

solid

Synonym(s):

R(−)-2-OH-NPA HBr, R(−)-TNPA HBr

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About This Item

Empirical Formula (Hill Notation):
C19H21NO3 · HBr · xH2O
CAS Number:
79640-85-0
Molecular Weight:
392.29 (anhydrous basis)
MDL number:
MFCD00069241
UNSPSC Code:
12352200
PubChem Substance ID:
24277903

form

solid

optical activity

[α]22/D −64°, c = 7 mg/mL in methanol(lit.)

color

light brown

solubility

alcohol: soluble (Solutions should be freshly prepared.)
aqueous acid: moderately soluble (Solutions should be freshly prepared)
aqueous base: insoluble

storage temp.

2-8°C

SMILES string

Br.[H][C@]12Cc3ccc(O)c(O)c3-c4cc(O)cc(CCN1CCC)c24

Gene Information

human ... DRD2(1813)

Biochem/physiol Actions

Potent, selective D2 dopamine receptor agonist.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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E A Jackson et al.
European journal of pharmacology, 87(1), 15-23 (1983-01-28)
The behavioral actions of some novel aporphines have been examined in rats with selective unilateral 6-hydroxydopamine (6OHDA)-induced destruction of nigrostriatal dopaminergic neurons, and in rats with bilateral 6OHDA-induced destruction of mesolimbic dopaminergic neurons. Dopaminomimetics such as apomorphine (APO) in these
Y G Gao et al.
Journal of medicinal chemistry, 33(6), 1800-1805 (1990-06-01)
Syntheses of (R)-(-)-2-methoxyapomorphine (R-8), its antipode S-8, and its (R)-(-)-N-n-propyl R-9 derivatives are described. The dopaminergic receptor affinities of these compounds and their 2-unsubstituted counterparts (R)-(-)-apomorphine (R(-)-APO, R-1), (S)-(+)-apomorphine (S(+)-APO, S-1), and (R)-(-)-N-n-propylnorapomorphine (R(-)-NPA, R-2), as well as those of
E Chu et al.
Experimental eye research, 69(6), 611-616 (2000-01-06)
The purpose of this study was to correlate potential mechanisms with site(s) of action for TNPA-induced ocular hypotension. In response to R(-)-2, 10, 11-trihydroxy-N-propyl-noraporphine hydrobromide (TNPA, 75 microg), a D2 dopamine receptor agonist, the intraocular pressure decreased by 4.5 and
J L Neumeyer et al.
Journal of medicinal chemistry, 24(7), 898-899 (1981-07-01)
(-)-2,10,11-Trihydroxy-N-n-propylnoraporphine (TNPA,2c) has been synthesized from thebaine (3a), via northebaine (3b), normorphothebaine (2a), and alkylation to the N-propyl derivative 2b. O-Demethylation gave the desired product 2c. Compound 2c showed activity comparable to its 10,11-dihyroxy counterpart (NPA, 1b) on the stimulation

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