(+)-Morphine

(+)-Morphine also known as dextro-morphine is the "unnatural" enantiomer of the opioid drug (−)-morphine. Unlike "natural" levo-morphine, unnatural dextro-morphine is not present in Papaver somniferum and is the product of laboratory synthesis.

CAS Number

• 65165-99-3 ^N

PubChem CID

• 5479215

ChemSpider

• 4586177 ^Y

FormulaC₁₇H₁₉NO₃

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(+)-Morphine

Identifiers
IUPAC name (4S,4aS,7R,7aS,12bR)-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
CAS Number	65165-99-3 N
PubChem CID	5479215
ChemSpider	4586177 Y
Chemical and physical data
Formula	C17H19NO3
Molar mass	285.343 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CC[C@@]23[C@H]4[C@@H]1CC5=C2C(=C(C=C5)O)O[C@@H]3[C@@H](C=C4)O
InChI InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m1/s1 Y Key:BQJCRHHNABKAKU-QHQPWPDESA-N Y

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In contrast to natural morphine, the unnatural enantiomer has no affinity or efficacy for the mu opioid receptor and therefore has no analgesic effects. To the contrary, in rats, (+)-morphine acts as an antianalgesic and is approximately 71,000 times more potent as an antianalgesic than (−)-morphine is as an analgesic.^[1] (+)-Morphine derives its antianalgesic effects by being a selective-agonist of the Toll-like receptor 4 (TLR4), which due to not binding to opioid receptors allows it to effectively reverse the analgesic properties of (−)-morphine. TLR4 is involved in immune system responses, and activation of TLR4 induces glial activation and release of inflammatory mediators such as TNF-α and Interleukin-1.^[2][3]