Editing Morphine (section)

===Chemical salts of Morphine===
{{More citations needed section|date=March 2021 |talk=Need for expert attention}}
Both morphine and its hydrated form<!-- , C<span style="font-size:100%;"><sub>17</sub></span>H<span style="font-size:100%;"><sub>19</sub></span>NO<span style="font-size:100%;"><sub>3</sub></span>H<span style="font-size:100%;"><sub>2</sub></span>O, THIS TYPE OF FORMULAIC REPRESENTATION IS ALMOST MEANINGLESS HERE; YOU WISH THE READER TO TAKE THE COMPARABLE FORMULA FOR THE ANHYDRATE, DO A SUBTRACTION, AND THEN FACTOR TO DETERMINE WHETHER IT IS A MONO_ OR HIGHER ORDER HYDRATE? **JUST STATE IT.** --> are sparingly soluble in water.<ref>{{cite book| vauthors = Loftsson T |url=http://worldcat.org/oclc/1136560730|title=Drug Stability for Pharmaceutical Scientists|publisher=Elsevier Science & Technology|year=2013|pages=82|oclc=1136560730}}</ref><!-- ABSENT TEMPERATURE, THE FOLLOWING STATEMENT IS MEANINGLESS; HERE IT IS FOR USE IN PLAGIARISM CHECKING OF THIS UNSOURCED SECTION: In five liters of water, only one gram of the hydrate will dissolve. --> For this reason, pharmaceutical companies produce sulfate and [[Hydrochloride|hydrochloride salts]] of the drug, both of which are over 300 times more water-soluble than their parent molecule.{{clarify|date=February 2020}}{{citation needed|date=February 2020}} Whereas the pH of a saturated morphine hydrate solution is 8.5, the salts are acidic.{{citation needed|date=February 2020}} Since they derive from a strong acid but weak base, they are both at about pH = 5;{{clarify|date=February 2020}}{{citation needed|date=February 2020}} as a consequence, the morphine salts are mixed with small amounts of [[Sodium hydroxide|NaOH]] to make them suitable for injection.{{citation needed|date=February 2020}}<!-- <ref name="urlMorphine">{{cite web |url = http://www.emsb.qc.ca/laurenhill/science/morphine.html |title = Morphine |website = LHA Science Page |publisher = LaurenHill Academy |url-status = live |archive-url = https://web.archive.org/web/20050215094332/http://www.emsb.qc.ca/laurenhill/science/morphine.html |archive-date = 15 February 2005 }}</ref> A HIGH SCHOOL WEB PAGE IS NOT AN APPROPRIATE SOURCE FOR THIS WIDELY STUDIED, AND UBUQUITOUSLY DESCRIBED, IMPORTANT MOLECULE. THE SAME IS TRUE AT ALL OCCURRENCES. AND PRESENTING A CITATION AT END OF PARAGRAPH IS ACTUALLY WORSE THAN PRESENTING NONE AT ALL< BECAUSE IT GIVES THE IMPRESSION THAT THE MATERIAL IS ADEQUATELY SOURCED, TO THE NAIVE READER. -->

Many salts of morphine are used, with the most common in current clinical use being the hydrochloride, sulfate, tartrate, and citrate;{{citation needed|date=February 2020}} less commonly methobromide, hydrobromide, hydroiodide, lactate, chloride, and bitartrate and the others listed below.{{citation needed|date=February 2020}} Morphine diacetate (heroin) is not a salt, but rather a further derivative,{{citation needed|date=February 2020}} see above.<ref>Heroin (morphine diacetate) is a Schedule I controlled substance, so it is not used clinically in the United States;{{citation needed|date=February 2020}} it is a sanctioned medication in the [[United Kingdom]] and in [[Canada]] and some countries in Continental Europe, its use being particularly common (nearly to the degree of the hydrochloride salt){{clarify|date=February 2020}} in the United Kingdom.{{citation needed|date=February 2020}}</ref>

Morphine meconate is a major form of the alkaloid in the poppy, as is morphine pectinate, nitrate, sulfate, and some others.{{citation needed|date=February 2020}} Like codeine, dihydrocodeine and other (especially older) opiates, morphine has been used as the salicylate salt by some suppliers and can be easily compounded, imparting the therapeutic advantage of both the opioid and the [[NSAID]];{{citation needed|date=February 2020}} multiple [[barbiturate]] salts of morphine were also used in the past, as was/is morphine valerate, the salt of the acid being the active principle of [[valerian (herb)|valerian]].{{citation needed|date=February 2020}} [[Calcium morphenate]] is the intermediate in various latex and poppy-straw methods of morphine production, more rarely sodium morphenate takes its place.{{citation needed|date=February 2020}} Morphine ascorbate and other salts such as the tannate, citrate, and acetate, phosphate, valerate and others may be present in poppy tea depending on the method of preparation.{{citation needed|date=February 2020}}<ref>Morphine valerate was one ingredient of a medication available for both oral and parenteral administration popular a number of years ago in Europe and elsewhere called Trivalin—not to be confused with the current, unrelated herbal preparation of the same name—which also included the valerates of [[caffeine]] and [[cocaine]].{{citation needed|date=February 2020}} A version containing codeine valerate as a fourth ingredient is distributed under the name Tetravalin.{{citation needed|date=February 2020}}</ref>

The salts listed by the [[United States Drug Enforcement Administration]] for reporting purposes, in addition to a few others, are as follows:{{citation needed|date=February 2020}}
{| class="talk collapsed collapsible"
|-
! Select salts of morphine with their [[Controlled Substances Act]] (CSA) schedule, [[Administrative Controlled Substances Code Number]] (ACSCN), and free base conversion ratio.{{clarify|date=February 2020}}{{citation needed|date=February 2020}}
|- style="text-align: left;"
|
{| class="wikitable"
|-
! Salt or drug !! [[Controlled Substances Act|CSA]] schedule !! [[Administrative Controlled Substances Code Number|ACSCN]] !! Free base conversion ratio
|-
| Morphine (base)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 1
|-
| Morphine citrate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.81
|-
| Morphine bitartrate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.66
|-
| Morphine stearate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.51
|-
| Morphine phthalate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.89
|-
| Morphine hydrobromide
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.78
|-
| Morphine hydrobromide (2 H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.71
|-
| Morphine hydrochloride
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.89
|-
| Morphine hydrochloride (3 H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.76
|-
| Morphine acetate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.71
|-
| Morphine hydriodide (2 H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.64
|-
| Morphine lactate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.76
|-
| Morphine monohydrate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.94
|-
| Morphine meconate (5 H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.66
|-
| Morphine mucate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.57
|-
| Morphine nitrate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.82
|-
| Morphine phosphate ({{frac|1|2}} H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.73
|-
| Morphine phosphate (7 H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.73
|-
| Morphine salicylate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
|
|-
| Morphine pectinate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.778
|-
| Morphine phenylpropionate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.65
|-
| Morphine methyliodide
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.67
|-
| Morphine isobutyrate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.76
|-
| Morphine hypophosphite
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.81
|-
| Morphine sulfate (5 H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.75
|-
| Morphine tannate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
|
|-
| Morphine tartrate (3 H<sub>2</sub>O)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.74
|-
| Morphine valerate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.74
|-
| Morphine diethylbarbiturate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.619
|-
| Morphine cyclopentylallylbarbiturate
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9300
| 0.561
|-
| Morphine diacetate
| [[Controlled Substances Act#Schedule I controlled substances|I]]
| 9200
| 0.74
|-
| Morphine methylbromide
| [[Controlled Substances Act#Schedule I controlled substances|I]]
| 9305
| 0.75
|-
| Morphine methylsulfonate
| [[Controlled Substances Act#Schedule I controlled substances|I]]
| 9306
| 0.75
|-
| Morphine-N-oxide
| [[Controlled Substances Act#Schedule I controlled substances|I]]
| 9307
| 1
|-
| Morphine-N-oxide quinate
| [[Controlled Substances Act#Schedule I controlled substances|I]]
| 9307
| 0.60
|-
| Morphine dinicotinate HCl (Nicomorphine)
| [[Controlled Substances Act#Schedule II controlled substances|II]]
| 9312
| 0.931
|}
|}