Levallorphan

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MedKoo CAT#: 318092

CAS#: 152-02-3

Description: Levallorphan, also known as levallorphan tartate (USAN), is an opioid modulator of the morphinan family used as an opioid analgesic and opioid antagonist/antidote. It acts as an antagonist of the μ-opioid receptor (MOR) and as an agonist of the κ-opioid receptor (KOR), and as a result, blocks the effects of stronger agents with greater intrinsic activity such as morphine whilst simultaneously producing analgesia. As an agonist of the KOR, levallorphan can produce severe mental reactions at sufficient doses including hallucinations, dissociation, and other psychotomimetic effects, dysphoria, anxiety, confusion, dizziness, disorientation, derealization, feelings of drunkenness, and bizarre, unusual, or disturbing dreams. (Source: https://en.wikipedia.org/wiki/Levallorphan).


Chemical Structure

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Levallorphan
CAS# 152-02-3

Theoretical Analysis

MedKoo Cat#: 318092
Name: Levallorphan
CAS#: 152-02-3
Chemical Formula: C19H25NO
Exact Mass: 283.19
Molecular Weight: 283.408
Elemental Analysis: C, 80.52; H, 8.89; N, 4.94; O, 5.65

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Levallorphan; Naloxiphan; Lorfan; Levallorphane; Levallorphanum; Levalorfano; levallorphan tartate

IUPAC/Chemical Name: (−)-17-allylmorphinan-3-ol

InChi Key: OZYUPQUCAUTOBP-QXAKKESOSA-N

InChi Code: InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1

SMILES Code: C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 283.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bonn B, Masimirembwa CM, Castagnoli N Jr. Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan. Drug Metab Dispos. 2010 Jan;38(1):187-99. doi: 10.1124/dmd.109.028670. Epub . PubMed PMID: 19797609.

2: Okamoto Y, Suzuki T, Murayama S. Effects of naloxone and levallorphan on the spinal cord reflex potentials under the spinal ischemic condition in cats. Jpn J Pharmacol. 1992 Aug;59(4):435-41. PubMed PMID: 1434139.

3: Handa N, Matsumoto M, Kitagawa K, Uehara A, Ogawa S, Etani H, Yoneda S, Kimura K, Kamada T. Levallorphan and dynorphin improve motor dysfunction in Mongolian gerbils with unilateral carotid occlusion: the first application of the inclined plane method in the experimental cerebral ischemia. Life Sci. 1988;42(19):1825-31. PubMed PMID: 2897055.

4: Bianchi G, Fiocchi R, Peracchia F, Petrillo P, Tavani A, Manara L. The peripheral narcotic antagonist N-allyl levallorphan-bromide (CM 32191) selectively prevents morphine antipropulsive action and buprenorphine in-vivo binding in the rat intestine. J Pharm Pharmacol. 1984 May;36(5):326-30. PubMed PMID: 6145770.

5: Dragonetti M, Bianchetti A, Sacilotto R, Giudice A, Ferrarese N, Cattaneo C, Manara L. Levallorphan methyl iodide (SR 58002), a potent narcotic antagonist with peripheral selectivity superior to that of other quaternary compounds. Life Sci. 1983;33 Suppl 1:477-80. PubMed PMID: 6664228.

6: Tagashira E, Izumi T, Yanaura S. Mode of antagonistic action of levallorphan in morphine-dependent rats and assessment of physical dependence liability. Jpn J Pharmacol. 1979 Aug;29(4):623-30. PubMed PMID: 575396.

7: Yamamoto M, Kumagai F, Tachikawa S, Maeno H. Lack of effect of levallorphan on analgesia induced by intraventricular application of porcine calcitonin in mice. Eur J Pharmacol. 1979 Apr 15;55(2):211-3. PubMed PMID: 456419.

8: Lal S, Nair NP, Cervantes P, Pulman J, Guyda H. Effect of naloxone or levallorphan on serum prolactin concentrations and apomorphine-induced growth hormone secretion. Acta Psychiatr Scand. 1979 Feb;59(2):173-9. PubMed PMID: 420037.

9: Frelat G, Boquet PL. Levallorphan-tolerant mutants of Excherichia coli with altered morphologies. J Bacteriol. 1979 Feb;137(2):1013-6. PubMed PMID: 370088; PubMed Central PMCID: PMC218387.

10: Dame JB, Shapiro BM. Use of polymyxin B, levallorphan, and tetracaine to isolate novel envelope mutants of Escherichia coli. J Bacteriol. 1976 Aug;127(2):961-72. PubMed PMID: 182670; PubMed Central PMCID: PMC233006.