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Morphine

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Name

Morphine

EINECS 200-320-2
CAS No. 57-27-2 Density 1.44 g/cm3
PSA 52.93000 LogP 1.13600
Solubility 0.4mg/L(25 oC) Melting Point 255°C
Formula C17H19NO3 Boiling Point 476.247 °C at 760 mmHg
Molecular Weight 285.343 Flash Point 241.826 °C
Transport Information N/A Appearance N/A
Safety 7-16-36/37-45 Risk Codes 11-23/24/25-39/23/24/25
Molecular Structure Molecular Structure of 57-27-2 (MORPHINE) Hazard Symbols FlammableF,VeryT+
Synonyms

Morphinan-3,6a-diol, 7,8-didehydro-4,5a-epoxy-17-methyl- (8CI);(-)-Morphine;Aguettant;DepoDur;Dimorf;Dinamorf;Dulcontin;Duromorph;M-Eslon;MS Contin;Meconium;Morphia;Morphin;Morphina;Morphine;Morphinism;Morphinum;Morphium;Nepenthe;Ospalivina;Sevredol;Statex SR;l-Morphine;

Article Data 55

Morphine History

The discovery of Morphine is analgesic activity in 1806 started a long series of studies of the alkaloids from the opium poppy, including morphine's first correctly postulated structure in 1925 and its total synthesis in 1952. The depressant action of the morphine group is the most useful property, resulting in an increased tolerance to pain, a sleepy feeling, a lessened perception to external stimuli, and a feeling of well being. Respiratory depression and addiction are its serious drawbacks.
It was announced in 1973 that a team at the National Institutes of Health in the United States had developed a method for total synthesis of morphine, codeine, and thebaine using coal tar as a starting material.
In 2003 there was discovery of endogenous morphine occurring naturally in the human body.

Morphine Specification

The Morphine, with the CAS registry number 57-27-2, is also known as Morphinan-3,6-alpha-diol, 7,8-didehydro-4,5-alpha-epoxy-17-methyl-. It belongs to the product categories of Chiral Reagents; Impurities; Intermediates & Fine Chemicals; Pharmaceuticals; Alkaloids Stable Isotopes; Chemical Structure; Controlled Drug Standards Alphabetic; Drugs of Abuse; M; METI - MZDrugs of Abuse; Morphine. Its EINECS registry number is 200-320-2. This chemical's molecular formula is C17H19NO3 and molecular weight is 285.34. Its IUPAC name is called (5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol.

Physical properties of Morphine: (1)ACD/LogP: 0.87; (2)ACD/LogD (pH 7.4): 0.043; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 10.535; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.719; (11)Molar Refractivity: 78.022 cm3; (12)Molar Volume: 197.647 cm3; (13)Surface Tension: 72.878 dyne/cm; (14)Density: 1.444 g/cm3; (15)Flash Point: 241.826 °C; (16)Enthalpy of Vaporization: 77.946 kJ/mol; (17)Boiling Point: 476.247 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25°C.

Morphine can be used as an analgesic to relieve: Pain associated with Chronic Pancreatitis; pain in myocardial infarction; pain in sickle cell crisis; pain associated with surgical conditions, pre- and postoperatively; pain associated with trauma; severe chronic pain, e.g., cancer; pain from kidney stones; severe back pain. What's more, Morphine can also be used: as an adjunct to general anesthesia; in epidural anesthesia or intrathecal analgesia; for palliative care; as an antitussive for severe cough; in nebulized form, for treatment of dyspnea, although the evidence for efficacy is slim; Evidence is better for other routes; as an antidiarrheal in chronic conditions; for relief of acute pulmonary edema through an unknown mechanism; for lowering and stabilising blood glucose in diabetics and combating other diabetic effects including diabetic neuropathy. Morphine and whole opium preparations were used for this purpose well into the 1960s in North America and Europe and in much curtailed fashion now and in other countries. Morphine will also impact hypertension, levels of lipids like cholesterol in blood, and improve laboratory indices in certain types of anaemia, although whole opium preparations are preferred for these purposes if allowed. Most often, chronic pain patients with one or more of the four above conditions are treated with morphine rather than synthetics like pethidine; experimentally for refractory depression. Morphine, hydromorphone, opium products and the like were used on-label for depression from antiquity or prehistoric time up into the middle 1950s. Even today, some doctors prescribe morphine and other opiates off label for depression, anxiety, and other mental illness. The dilemma is that a lifetime of treatment, sometimes with increasing doses, is required in these cases.

When you are using this chemical, please be cautious about it as the following:
This chemical may catch fire in contact with air and only need brief contact with an ignition source which has a very low flash point or evolve highly flammable gases in contact with water. Besides, this chemical that at low levels can cause damage to health. It is toxic by inhalation, in contact with skin and if swallowed. Whenever you will contact it, please wear suitable protective clothing and gloves. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: CN1CC[C@]23c4c5ccc(c4O[C@H]2[C@H](C=C[C@H]3[C@H]1C5)O)O
(2)InChI: InChI=1/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-/m0/s1
(3)InChIKey: BQJCRHHNABKAKU-KBQPJGBKBH

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 40mg/kg (40mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
chicken LDLo subcutaneous 900mg/kg (900mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
dog LD50 intravenous 133mg/kg (133mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 7, Pg. 372, 1959.
dog LDLo subcutaneous 210mg/kg (210mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
duck LDLo subcutaneous 900mg/kg (900mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
frog LDLo subcutaneous 600mg/kg (600mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1368, 1935.
guinea pig LDLo subcutaneous 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1367, 1935.
infant TDLo intravenous 100ug/kg (0.1mg/kg) CARDIAC: PULSE RATE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Journal of Hospital Pharmacy. Vol. 51, Pg. 2801, 1994.
mammal (species unspecified) LD50 intraperitoneal 380mg/kg (380mg/kg)   United States Patent Document. Vol. #4205173,
man LDLo unreported 3676ug/kg (3.676mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 3857ug/kg/1W- (3.857mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Lancet. Vol. 2, Pg. 98, 1987.
mouse LD50 intracrebral 6900ug/kg (6.9mg/kg)   Science. Vol. 134, Pg. 1078, 1961.
mouse LD50 intraperitoneal 140mg/kg (140mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 56S, 1957.
mouse LD50 intravenous 135mg/kg (135mg/kg)   Therapie. Vol. 7, Pg. 21, 1952.
mouse LD50 oral 524mg/kg (524mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
mouse LD50 subcutaneous 220mg/kg (220mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 25, 1958.
mouse LD50 unreported 500mg/kg (500mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 67(4), Pg. 97P, 1971.
pigeon LDLo oral 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1368, 1935.
pigeon LDLo subcutaneous 250mg/kg (250mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LDLo intravenous 8mg/kg (8mg/kg)   Agents and Actions, A Swiss Journal of Pharmacology. Vol. 3, Pg. 28, 1973.
rabbit LDLo subcutaneous 190mg/kg (190mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rat LD50 intraperitoneal 100mg/kg (100mg/kg)   European Patent Application. Vol. #0047990,
rat LD50 intravenous 140mg/kg (140mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 7, Pg. 196, 1952.
rat LD50 oral 335mg/kg (335mg/kg)   Drugs of the Future. Vol. 2, Pg. 39, 1977.
rat LD50 subcutaneous 109mg/kg (109mg/kg)   Pharmaceutical Chemistry Journal Vol. 23, Pg. 395, 1989.
rat LD50 unreported 134mg/kg (134mg/kg)   Farmakologiya i Toksikologiya Vol. 39, Pg. 14, 1976.
women TDLo intramuscular 152ug/kg (0.152mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA International Journal of Clinical Pharmacology, Therapy and Toxicology. Vol. 30, Pg. 202, 1992.
women TDLo intravenous 1458ug/kg/C (1.458mg/kg) BEHAVIORAL: SLEEP

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
British Medical Journal. Vol. 309, Pg. 1002, 1994.