12
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The puzzle is to find pairs of English words (A,B) such that A and B are both synonyms and anagrams of each other.

For example, theater and theatre (which are the British and American spelling of the same word), and note and tone which mean both the same in music and are also anagrams of each other

To avoid making this too broad and to avoid trivial examples like (theater, theatre), let's define the score of the pair to be the number of places where the letters of the words differ. For example, for (theater, theatre) the score is 2, since the last letter differs (r versus e) and the next to last letter also differs (e versus r). For (note, tone), the score is also 2, since the first letter differs (n versus t) and the third also (t versus n). You're looking with the pair of words with the highest possible score.

Note: This question is inspired by Words that are anagrams of themselves by user stib.

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10
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8

alchemic chemical

Both mean something pertaining to the science, broadly defined.

anaesthesis anesthesias

Both mean absence of feeling, but are different transliterations off Latin.

depilate epilated

Both mean "having no hair".

10

headspring springhead

Both mean "source".

Allowing for pluralization changes

8

accoustrement accoutrements
synaesthesis synesthesias

13

imperceptions misperception

Swapping parts of words

8

outbreak breakout
hairbreadths hairsbreadth
handbreadths handsbreadth
macrophotograph photomacrograph
microphotograph photomicrograph

9

phototelegraph telephotograph

11

electrothermic thermoelectric

12

electromagnetic magnetoelectric

If we indulge ourselves in medical terminology, the scores can get very high:

14

encephalomeningitis meningoencephalitis

15

duodenopancreatectomy pancreatoduodenectomy

17

anatomicophysiologic physiologicoanatomic

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  • $\begingroup$ 'imperceptions' = 'misperception'? $\endgroup$ – smci Oct 24 '16 at 3:47
9
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Score of 3

  • it's vs 'tis (actually a score of 4 if you count punctuation)

Score of 4

  • evil vs vile

  • angered vs enraged

  • detail vs dilate (both can mean to talk at length and in detail)

Hat tip to Benjamin Kuykendall for a list of anagram-synonyms (he also includes several more which I felt were not close enough synonyms to include, such as name vs mean or punks vs spunk).

If you want to 'cheat' a little more by including words which are anagrams merely by having parts of them swapped around, we can get larger scores ...

Score of 5

  • sergeants-major vs sergeant-majors (both seem to be acceptable plurals)

Score of 6

  • lookout vs outlook

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  • $\begingroup$ How many milli seconds was the difference? $\endgroup$ – Sid Oct 23 '16 at 15:19
  • $\begingroup$ @Sid I was 3 seconds faster :-) $\endgroup$ – Rand al'Thor Oct 23 '16 at 15:20
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    $\begingroup$ Why not just live = evil ;) $\endgroup$ – Avigrail Oct 23 '16 at 22:11
4
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I (thought that I had) found a 10:

  • identifiably, definability = $10$

Both mean that something can be identified or defined (Unfortunately I read identifiably as identifiability, so this doesn't count)

I have some smaller ones too:

  • cleaners, cleanser = $3$
  • detail, dilate = $4$
  • parental, paternal = $3$
  • recourse, resource = $2$
  • vileness, evilness = $4$
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  • $\begingroup$ The highest-scoring among these are detail/dilate and vileness/evilness, both of which are already in my answer :-) Are you using the same (ELU) source as I found? $\endgroup$ – Rand al'Thor Oct 23 '16 at 15:31
  • $\begingroup$ @randal'thor probably :P $\endgroup$ – Beastly Gerbil Oct 23 '16 at 15:31
  • $\begingroup$ @randal'thor think I found a 10 though $\endgroup$ – Beastly Gerbil Oct 23 '16 at 15:37
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    $\begingroup$ Those aren't synonyms: one of them is an adverb and the other is a noun. $\endgroup$ – Rand al'Thor Oct 23 '16 at 15:41
  • $\begingroup$ @randal'thor aaaah I read identifiably as identifiability. Oops $\endgroup$ – Beastly Gerbil Oct 23 '16 at 15:43
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Here's what I found

Vile and Evil (The Score is 4, if I got the rules correctly)
Team and Mate (Not exactly synonyms, but close) -Score of 4

And further answers as found

Dilate and detail (Score is 4 for this as well)

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