InChI=1/C17H21NO3/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/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1

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Search term: IJVCSMSMFSCRME-KBQPJGBKBC
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Inherent Properties, Identifiers and References

ChemSpider ID:	4514282
Empirical Formula:	C₁₇H₂₁NO₃
Molecular Weight:	287.3535
Nominal Mass:	287 Da
Average Mass:	287.3535 Da
Monoisotopic Mass:	287.152144 Da

Systematic Name:

SMILES:

O[C@@H]4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@H]3CC4)C

InChI:

InChI=1/C17H21NO3/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/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1

InChIKey:

IJVCSMSMFSCRME-KBQPJGBKBC

Std. InChI:

InChI=1S/C17H21NO3/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/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1

Std. InChIKey:

IJVCSMSMFSCRME-KBQPJGBKSA-N

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Wikipedia Article(s)

Dihydromorphine (Paramorfan, DHM, Paramorphan) is a semi-synthetic opioid invented in Germany in 1900. In structure, it is very similar to morphine, the only difference being the reduction of the double bond between positions 7 and 8 in morphine to a single bond. Dihydromorphine can be made by several processes, including hydrogenating morphine or opium or by demethylating either dihydrocodeine or tetrahydrothebaine. Dihydromorphine is available as tablets for oral use, ampoules of solution for injection by various routes, suppositories, and liquids for oral and sublingual use. Dihydromorphine is slightly stronger than morphine as an analgesic with a similar side-effect profile. Like metopon, dihydromorphine may be less addictive overall and have better bioavailability after oral administration than morphine. The onset of action is more rapid than morphine and it also tends to have a longer duration of action, generally 4–7 hours. Other drugs with faster onset of action such as nicomorphine and hydromorphone also tend to wear off more quickly, with a mean duration of action around 3 hours in most patients. At the present time, dihydromorphine is most commonly used in Japan, and various European and Asian countries. A United Nations report in 1993 stated increases in use of dihydromorphine in some Central European countries, and, later, WHO and EU reports show the same, although distinction is not made between use of Paramorfan as an analgesic product or the use of dihydromorphine in the manufacture of other drugs. The latter is also the case in the United States, where it is seen exclusively as an intermediate in the manufacture of dihydrocodeine as well as in some methods of manufacture of hydrocodone, hydromorphone, and related drugs. It is available as the hydrochloride, hydroiodide, or monohydrate salt, with the former being the form almost exclusively used in pharmaceuticals but the hydroiodide also used especially in making dihydrocodeine hydroiodide (Paracodin). Individuals and organisations are lobbying for the United States to legalise and approve dihydromorphine for use alongside other analgesics. The Usenet newsgroup alt.politics.usa.legalise-dihydromorphine is one example, albeit atypical in its post volume and pattern. Dihydromorphine was never introduced in the United States, as is the case of many similar drugs invented in Europe in the intense search for stronger cough suppressants, especially to slow the spread of tuberculosis and other airborne diseases in the two decades prior to the First World War such as thebacon, nicomorphine (Vilan), benzylmorphine (Peronine), dihydroisocodeine, acetylmorphone, diacetylmorphine (heroin), nicocodeine, acetyldihydrocodeine, nicodicodeine, and others. For this reason, in the United States, dihydromorphine shares a Schedule I designation with these other opioids, under the Controlled Substances Act of 1970. In most other countries, dihydromorphine is classified at the same level as morphine, pethidine and the like where it is available and used; international law and treaties list it as a narcotic subject to control, and other countries' laws may vary. Its role in the production of dihydrocodeine makes it the Schedule I substance with one of the higher annual manufacturing quotas granted by the US Drug Enforcement Administration. One scientific controversy deals with the relative strength of dihydromorphine; according to various official sources, is either 50 per cent or 115-120 per cent of the analgesic strength of morphine. Clinical experience points to the latter. In comparison, dihydrocodeine is 1½ times the strength of codeine but also differs from codeine in not having a ceiling effect on analgesia imposed by metabolism—i.e., above a certain point (400 mg in most people), the codeine is wasted. Dihydromorphine has a longer duration of action (6 hours vs 4 hours for morphine). Dihydromorphine, often labelled with the isotopes iodine-129 and tritium, was amongst tools utilised in the 20th century research, which eventually led to the theory and discovery of opioid receptors in the human nervous system. Other opioids like buprenorphine, morphine and others are similarly used for research on the actions of drugs of this type in various systems of the body. The human liver converts a percentage of dihydrocodeine into dihydromorphine. The liver enzymes of the cytochrome P450 II-D-6 series accomplish this feat in a way similar to which the liver activates codeine, by demethylating it to morphine (also, hydrocodone to hydromorphone, oxycodone to oxymorphone, nicocodeine to 6-nicotinoylmorphine, and so on). Other derivates or analogues of dihydromorphine are the dihydrocodeine-related family of moderate painkillers and effective cough suppressants (thebacon, nicocodeine, acetyldihydrocodeine, nicodicodeine, and others.) Category:Opioids ru:Дигидроморфин sv:Dihydromorfin Read more... or Edit at Wikipedia...

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Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(5a,6a)-4,5-Epoxy-17-methylmorphinan-3,6-diol

(5alpha,6alpha)-17-Methyl-4,5-epoxymorphinan-3,6-diol

208-100-8 [EINECS/ELINCS]

509-60-4 [RN]

Morphinan-3,6-diol, 4,5-epoxy-17-methyl-, (5.alpha.,6.alpha.)-

morphinan-3,6-diol, 4,5-epoxy-17-methyl-, (5alpha,6alpha)-

509-60-4

6-alpha-Hydromorphol

7,8-dihydromorphine

Dihydromorfin [Czech]

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Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

ACD/Labs Predicted Properties

ACD/LogP:	0.62	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-2.05	ACD/LogD (pH 7.4):	-0.4
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	1	ACD/KOC (pH 7.4):	4.93
#H bond acceptors:	4	#H bond donors:	2
#Freely Rotating Bonds:	2	Polar Surface Area:	30.93 Å²
Index of Refraction:	1.69	Molar Refractivity:	78.11 cm³
Molar Volume:	204.3 cm³	Polarizability:	30.96 10^-24cm³
Surface Tension:	69.4 dyne/cm	Density:	1.4 g/cm³
Flash Point:	241.3 °C	Enthalpy of Vaporization:	77.83 kJ/mol
Boiling Point:	475.4 °C at 760 mmHg	Vapour Pressure:	7.65E-10 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.93

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  415.38  (Adapted Stein & Brown method)
    Melting Pt (deg C):  173.07  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.91E-009  (Modified Grain method)
    MP  (exp database):  157 dec deg C
    Subcooled liquid VP: 6.53E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  2.376e+004
       log Kow used: 0.93 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10278 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.51E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.631E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.93  (KowWin est)
  Log Kaw used:  -14.209  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.139
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6827
   Biowin2 (Non-Linear Model)     :   0.4586
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1806  (months      )
   Biowin4 (Primary Survey Model) :   3.1694  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3505
   Biowin6 (MITI Non-Linear Model):   0.0556
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8960
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  8.71E-006 Pa (6.53E-008 mm Hg)
  Log Koa (Koawin est  ): 15.139
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.345 
       Octanol/air (Koa) model:  338 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.926 
       Mackay model           :  0.965 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 213.6320 E-12 cm3/molecule-sec
      Half-Life =     0.050 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.601 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.945 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2968
      Log Koc:  3.473 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.93 (estimated)

 Volatilization from Water:
    Henry LC:  1.51E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.573E+012  hours   (2.739E+011 days)
    Half-Life from Model Lake :  7.17E+013  hours   (2.988E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       1.88e-008       1.2          1000       
   Water     44              1.44e+003    1000       
   Soil      55.9            2.88e+003    1000       
   Sediment  0.0929          1.3e+004     0          
     Persistence Time: 1.27e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 3, 0, 0, 2, 4, 9, 2, 8, 0, 6, 0, 0, 0, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Metalloenzymes	ADA, adenosine deaminase	1stw	0.02
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.02
Kinases	TK, thymidine kinase	1kim	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Serine Proteases	Thrombin	1ba8	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Serine Proteases	Trypsin	1bju	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00

Spectra