ORGANIC CHEMISTRY LECTURE – OCH 1301

EZEKIEL P. ESCOBAR | MS. ADDIE ALBANO | PLM BSPT 1-7

AUGUST 23, 2021

MORPHINE
An opiate analgesic used to treat severe pain.

2D Structure 3D Conformer Crystal Structure

(Ball-and-stick)

a. What is the molecular formula and molecular weight of the compound?

Molecular Formula C17H19NO3
Molecular Weight Average: 285.3377
Monoisotopic: 285.136493479

b. What is the hybridization of each carbon atom? Label the structure.

sp3
(9) Carbon atoms
are sp3 hybridized.
On the other hand, (8)
carbon atoms are sp3
sp hybridized.
2 sp3

sp2 sp2 sp
3
sp2
sp 3
sp3
sp2 sp2
sp2
sp3
sp3
sp2
sp2 sp3

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c. What is the IUPAC name of the compound?

(4R,4aR,7S,7aR,12bS)-3-methyl-
IUPAC name 2,4,4a,7,7a,13-hexahydro-1H-4,12-
methanobenzofuro[3,2-e]isoquinoline-
7,9-diol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

d. Indicate the polar part(s) of the molecule by indicating δ+ and δ- in the appropriate
locations and indicate the direction of the dipole moment.
δ+

δ-

δ+
δ+

δ+
δ+ δ+ δ- δ+
δ-
δ+ δ- δ+

e. What is the boiling and melting point of the compound? Compare it to the BP and MP
of Phenathrene: BP=338.4°C, MP=99°C
Boiling Point 255ºC
Melting Point 190ºC
Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene
rings which takes its name from the two terms 'phenyl' and 'anthracene.' Phenanthrene appears
as colorless monoclinic crystals with a faint aromatic odor. Solutions exhibit a blue
fluorescence. It has a role as an environmental contaminant and a mouse metabolite.

The boiling point of Phenathrene (338.4°C) is much higher than the boiling point of
Morphine (255ºC). On the other hand, Morphine has higher melting point (190ºC) compared to
the melting point of Phenathrene (99ºC).

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f. Physical description of the compound

Physical Description Solid
Boiling Point 190ºC
Melting Point 255ºC
Color/Form Prisms; White, crystalline alkaloid; Small
rhombic prisms or needles from dilute
alcohol; slightly yellow during storage
Odor Odorless
Taste Bitter
Solubility 149 mg/L (at 20°C)
Slowly soluble in water, difficult soluble in
alcohol, and very slightly soluble in
chloroform and ether
Density 1.32 at 20°C/4°C
Vapor Pressure 1.8X10-10 mm Hg at 25°C (est.)
Lipophilicity (LogP) 0.89
Henry’s Law Constant Henry's Law constant = 1.33X10-16 atm-
cu m/mol at 25°C (est.)
Stability/Shelf Life When exposed to air, morphine
sulfate gradually loses its water of
hydration. The drug darkens on prolonged
exposure to light.
Optical Rotation Yellowish-white powder;
slight acetic odor. Specific optical rotation
(15°C): 77 deg (water). One g dissolves in
2.25 m: water, 2 m\L boiling water, 22 mL
alcohol, 2 mL alcohol at 60°C, 4.5
mL glycerol, 4.75 mL chloroform.
Practically insoluble in ether.

Specific optical rotation: -132 deg at

25°C/D (methanol)
Decomposition When heated to decomposition it emits
toxic fumes of nitrogen oxide.
pH pH of saturated solution: 8.5
pKa (Acid dissociation constant) pKa = 8.21 at 25°C; pKa = 9.85 at 20°C
Collision Cross Section 164 Ų [M+H]+ [CCS Type: TW, Method:
Major Mix IMS/Tof Calibration Kit
(Waters)]
Other Experimental Properties Occurs as the trihydrate. White flakes or
crystalline powder; bitter taste. Loses
its water of crystallization at about 100°C
and usually becomes yellowish.
Morphine is legally available only in the form of its water-soluble salts. Most common are
morphine sulfate and morphine hydrochloride. Both are fine white crystalline powders,
bitter to the taste. Both are soluble in water and slightly soluble in alcohol.
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g. Description of the compound

Morphine is a DEA controlled drug and a DEA Schedule II controlled substance.
Substances in the DEA Schedule II have a high potential for abuse which may lead to severe
psychological or physical dependence. Morphine is classified by the DEA as a Narcotics
(Opioids) drug. Street names for Morphine are Dreamer, Emsel, First Line, God’s Drug,
Hows, MS, Mister Blue, Morpho, and Unkie. (Drug Enforcement Administration)

Morphine is an opiate alkaloid isolated from the plant Papaver somniferum and
produced synthetically. Morphine binds to and activates specific opiate receptors (delta,
mu and kappa), each of which are involved in controlling different brain functions. In the
central nervous and gastrointestinal systems, this agent exhibits widespread effects
including analgesia, anxiolysis, euphoria, sedation, respiratory depression, and
gastrointestinal system smooth muscle contraction. (NCI Thesaurus)

Morphine is one of the natural plant alkaloids found in opium and is the prototype
opiate, against which other derivatives are measured in terms of analgesic effects and side
effects. Morphine has not been linked to serum enzyme elevations during therapy or to
clinically apparent liver injury. (LiverTox)

h. Application of the compound

Brand Names: Arymo, Avinza, Doloral, Duramorph, Embeda, Infumorph, Kadian, M-ediat, M-
eslon, MSIR, Mitigo, Ms Contin, Statex

Generic Name: Morphine

Morphine belongs to a class of drugs known as opioid analgesics. It works in the brain to
change how your body feels to manage chronic, moderate to severe pain. Opioids are effective
for the short-term management of pain. However, this may harm or cause death to other
people who take medication, especially children or other individuals taking it without a
prescription. Long term patients taking opioids may need to be monitored for the development
of physical dependence, addiction disorder, and drug abuse. Thus, medication should be kept
in safe place so no one else can take it accidentally or on purpose. Moreover, dispose any unneeded
morphine capsules, tablets, or liquid properly.

Depending on the specific product, this medication is given by injection into a vein, into a
muscle, or under the skin. Preservative-free morphine may also be given by a doctor as an
injection into the area around the spinal cord (epidural) or into the fluid-filled space that
contains the spinal cord (intrathecal). In this case, the medication is first given in the hospital
where you can be monitored closely. If the doctor directs you to continue using this medication at
home, it is usually given as a continuous injection using an infusion pump placed under the
skin.

This medicine is available only under a restricted distribution program called the
Opioid Analgesic REMS (Risk Evaluation and Mitigation Strategy) program. This product is
available in the following dosage forms:

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• Tablet, Extended Release

• Tablet
• Capsule, Extended Release, 24 HR
• Solution
• Capsule, Extended Release

Avinza, Kadian, and MorphaBond are examples of morphine brand products indicated for
the management of pain severe enough to require daily, around-the-clock, long-term
opioid treatment and for which alternative treatment options are inadequate.

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Other commercial products with Morphine:

Product Name:
Morphine Sulfate

Empirical Formula (Hill Notation):

C34H40N2O10S · 5H2O

Product Description:
British Pharmacopoeia (BP) Reference Standard

Price:
SGD 370.00
Product Name:
d3-Morphine

Empirical Formula (Hill Notation):

C17H16D3NO3

Product Description:
NMI Australia

Price:
SGD 338.00
Product Name:
Morphine sulfate Related Compound B

Empirical Formula (Hill Notation):

C34H36N2O6

Product Description:
United States Pharmacopeia (USP) Reference
Standard

Price:
SGD 338.00
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Product Name:
10-Hydroxynaltrexone solution

Empirical Formula (Hill Notation):

C20H23NO5

Product Description:
100 μg/mL in methanol, ampule of 1 mL, certified
reference material, Cerilliant®

Price:
SGD 1,210.00

REFERENCES:

Morphine (Oral Route) Description and Brand Names - Mayo Clinic. (2021). Mayoclinic.org;
https://www.mayoclinic.org/drugs-supplements/morphine-oral-route/description/drg-20074216

Morphine Abuse | Plugging, Snorting, Smoking, & Injecting Morphine. (2021, March 5). ARK
Behavioral Health. https://www.arkbh.com/opioids/morphine/abuse/

Morphine Injection: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD. (2021).
Webmd.com. https://www.webmd.com/drugs/2/drug-3891/morphine-injection/details

Morphine. (n.d.). Drugs.com. https://www.drugs.com/morphine.html

Morphine: MedlinePlus Drug Information. (2021, July). Medlineplus.gov.
https://medlineplus.gov/druginfo/meds/a682133.html

Morphine: Uses, Interactions, Mechanism of Action | DrugBank Online. (2017). Drugbank.com;

DrugBank. https://go.drugbank.com/drugs/DB00295

PubChem. (2021). Morphine. @Pubchem; PubChem.

https://pubchem.ncbi.nlm.nih.gov/compound/Morphine

PubChem. (2021). Phenanthrene. @Pubchem; PubChem.

https://pubchem.ncbi.nlm.nih.gov/compound/Phenanthrene#section=Melting-Point

Quotes about Organic chemistry (55 quotes). (2021). Quotemaster.org.

https://www.quotemaster.org/organic+chemistry

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The Effects of Mixing Morphine and Alcohol. (2020). Alcohol.org. https://www.alcohol.org/mixing-
with/morphine/

Timeline of Selected FDA Activities and Significant Events Addressing Opioid Misuse and Abuse .
(n.d.). https://www.fda.gov/media/106638/download

Zawn Villines. (2020, April 2). Morphine: How long does it stay in the

system? Medicalnewstoday.com; Medical News Today.

https://www.medicalnewstoday.com/articles/how-long-does-morphine-stay-in-the-system

Submitted By:

Ezekiel P. Escobar

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